Training Tim Ch. 02: Oral Exams

Chapter one gives a lot of character development and background that will not be repeated here. This can be a stand alone story but is probably better enjoyed with the first chapter having been read beforehand. All characters are above the age of eighteen when any sexual activity takes place.

*****

"The time has come to step up our training." Tonya said to Rebecca and Doris four weeks after Timmy's training had begun.

The three women were sitting around the kitchen table at Rebecca's apartment. Timmy had been sent out for bagels on this Saturday morning so that the women could plan the furtherance of his sexual education without being inhibited by his presence.

Rebecca had called the meeting and she agreed with Tonya's assessment. Timmy had done remarkably well in learning the ins and outs of pleasing a woman with his hands and fingers. For such a strong boy he was very gentle.

"What do you think Doris?" Rebecca asked her fifty six year old next door neighbor.

"What do I think? I'm not sure I'm qualified to answer that. When you first brought me into this project I was willing, no, actually eager to help with the sexual initiation and training of our late dear friend Suzanne's son. I think I was so eager because I was so horny. I'm not sure anymore if it was, if it is, the right thing to do."

"What do you mean, the right thing to do?" Tonya asked the older woman. "This was what his mother wanted. What she explicitly asked Rebecca here to arrange. We are helping him to develop skills which will make him a wonderful partner for one or many future lovers."

"But I feel like such a pervert. Cradle robber and all. My God, I have two sons who are almost fifteen years older than he is. I'm old enough to be his grandmother and the last time he was over at my place he was begging me to let him put his cock inside me."

"You didn't let him, did you?" Rebecca asked, and then added. "We were going to talk about when it was time for him to learn the fine art of cunnilingus and Tonya thinks that time has arrived. I agree. If you don't want to continue, I for one will understand. Just know that you have been so very helpful to this point Doris. You were a wonderful support emotionally to young Timmy when his mom passed."

"I don't want to quit on him now. I'm just feeling a little guilty. I haven't had sex since my husband Frank died five years ago and when I saw and then touched Timmy's cock I was hooked. Nevertheless I feel like I'm depriving some young girl of her due rights to be his first and warping him in some way."

"Fuck the young girls." Tonya said. "They don't know shit about sex and we do. As far as being first, that ship has sailed. We are going to be his firsts in many firsts and it will benefit him in the long run."

At thirty nine and the youngest of the three, Tonya had the most experience in this area. She pulled no punches when it came to her sexual appetite and confidence.

"You never answered Rebecca's question about whether you let the boy into your pussy or not."

"I did not. I was very tempted but I did not. I have been giving my big dildo quite the workout and Timmy has gotten very good at using three and sometimes four fingers to masturbate me. You have to remember that even though it was quite some time ago I did give birth twice and my vagina stretched some as a result. The size of that boys cock is just like my big boy toy. I have refrained from sampling it though. I can and will wait. I suppose you are right. I will get over my guilt."

"Yes Doris, I think you should get over your guilt." Said Rebecca. "Tonya is right that what we are doing will benefit him in the long run but let's be honest here. It will benefit us plenty in the short run. I, for one, am eager to taste that lovely dick."

"Ok then." Said Tonya. "We are agreed. Pussy eating fundamentals begin today. I think that aunt Becca should be the first to be serviced. Doris?"

"Yes, of course. It should be Rebecca first. Suzanne would have liked that. I'm going to make myself scarce now because I suspect you two are likely to offer some practical demonstration to the boy and I'd just as soon skip that visual. I'll be happy to let him sample my pussy after you have trained him up some."

"Oh Doris." Tonya said teasingly. "You are such the prude. You really need to experience a woman's practiced tongue on your little kitty sometime. You don't know what you're missing out on."

"No thanks ladies. I'm too old a kitty to learn those new tricks. Going home now. Have fun. I'm sure he will."

******

Timmy arrived back with the bagels to find only two of his special aunts were still in the apartment.

"They were all out of poppyseed." He said.

"That's ok Timmy. It was aunt Doris who wanted the poppyseed and she went back home. If you're not especially hungry right now and can wait awhile to eat, your aunt Tonya and I have something we wanted to talk with you about." Rebecca said.

"Ok." Timmy replied and sat down with the bag of bagels in his lap.

"Well, it's like this." Rebecca continued. "We have all been so very pleased with the way you have taken to your lessons on masturbation and pleasing us manually. The three of us have had a discussion and we agree it's time for you to learn new things."

"Oh boy! Does that mean I get to put my penis inside you now. I'll be gentle."

"No it does not, at least not for now." Rebecca said.

"What it means." Tonya said. "Is that you need to learn how to go down on a woman. How to give her head and enjoy doing it. There are few things that are more of a turn off than someone who doesn't know how to and doesn't enjoy giving head."

"Now a woman knows best how to pleasure a pussy but all women react and respond differently." Rebecca said. "Aunt Tonya is going to show you how I like to have my pussy eaten and you are going to watch and learn. You shouldn't take your cock out and play with it for the first few lessons because that might distract you."

"Why don't we all go back to the bedroom where we can be more comfortable?" Tonya offered as she led the way while unbuttoning her blouse.

Once in the bedroom Rebecca and Tonya both stripped and got on top of the king sized bed. Timmy was allowed to strip to his boxer briefs but was told by Rebecca to keep those on.

Tonya said to the boy. "I want you to move around and get as good a view as you can from as many angles as you can. This is going to be a very thorough demonstration."

"Ok aunt Tonya." Timmy eagerly agreed. It was strangely erotic and erection inducing for him to be calling her aunt Tonya when she wasn't even remotely related to him the teen thought to himself. In fact, referring to all three of the older women who had been masturbating him and allowing him to play with and masturbate them aunt was rather strange on the face of it. Aunt Becca, aunt Tonya, and aunt Doris were not aunts at all, at least not to him. They might be aunts to somebody and he knew Doris was actually a grandmother but he was not going to complain about the inaccuracy of his calling them that. They seemed to get extra excited by the additional illicitness of the make belief relationship and he did as well. His excitement was evidenced by the erection straining against the waistband of his boxer briefs. He was determined not to touch it because he knew that if he were a good student for this lesson he would be rewarded with an exquisite hand job by one or perhaps both of the lovely ladies lying naked before him.

Tonya leaned over Rebecca's breasts and began to kiss and suckle on one. She motioned for Timmy to do the same to the other and he did. The boy had become very adept at breast stimulation under his three aunts' tutelage and Rebecca was soon writhing with delight. Tonya then kissed and licked her way down aunt Becca's body until she was face down between her silken thighs and darting her tongue out playfully at her friend's engorged clit.

Timmy positioned himself to get as good a view as possible and looked up at aunt Becca once or twice to see the look of pleasure on her face. He wanted to be able to give her that pleasure. He saw the framed photo of his mother and Rebecca on the nightstand and had an image enter his head of his mom lathering away at aunt Becca's pussy just as Tonya was now doing. Instead of revolting him it made him hornier.

"Why don't you try for awhile?" Tonya said to him. Then she kissed him so that he could taste Rebecca's juices.

Timmy got down and immediately and eagerly began to slobber all over aunt Becca's pussy. He was very enthusiastic but still quite clueless as to the nuances of cunnilingus.

Rebecca then struck upon an idea which would shorten the learning curve for the boy.

"Timmy. Let Tonya do me again and you watch."

"Ok aunt Becca." He said, a little disappointed.

"While you are watching I'm going to take your hand and I want you to make a fist with it. You'll understand in a minute what I'm trying to do."

Timmy offered his hand and Rebecca formed the fist. She then touched the place where the middle finger met the back of his hand and the most prominent knuckle protruded.

"I'm going to make belief this is my clit." She said, and then continued. "I'm going to make belief this is my slit." Rebecca traced the space between the middle and index fingers of the teens right hand when she said this.

"Now while Tonya is eating my pussy I'm going to mimic what she is doing to me on your hand. That way you will get a sense of the pressure and pace of her wonderful tongue action."

"Why thank you sweetie." Tonya interjected. "You say the nicest things to a lady getting ready to give you the O face."

"You're welcome honey, now please get to work. I'm so horny I could climb the walls."

Tonya then trailed kisses up the thighs of her slender brunette friend and wound up licking the quickly moistening folds of her labia. Rebecca did the same to Tim's fist and when Tonya took time to work on her clit Tim felt auntie Becca's tongue dance on his knuckle. Up and down, side to side, and swirling around it, Tonya's talented tongue and lip action was replicated on Timmy's middle knuckle. Rebecca pursed her lips around it creating suction and continued to lather and lap at it with variations in pressure and technique. Timmy observed auntie Becca's hips hunching up towards Tonya's munching mouth and her breathing was becoming more rapid. Tonya reached up with one hand to fondle a boob while her other hand slid a couple of fingers into Rebecca's snatch. She motioned for Timmy to attend to the other boob and he did, circling and sucking on the nipple just as Rebecca was doing to his knuckle.

Rebecca eventually could concentrate no more on her instruction and succumbed to her own impending orgasm.

"Ooh! Yes! Yes! Right there! Yes!"

She began to shudder in waves and her thighs spasmed on either side of Tonya's face. Timmy was fascinated by her release. He had seen auntie Becca come before, sometimes by his own hand, but never with this level of abandon.

"Wow auntie Becca, you really came from that." Timmy said to her when she seemed capable of hearing the message.

"She sure did." Tonya said. "She is a real glutton for good head and your mom was the best. I try, but can't hold a candle to what she was able to do in so far as eating pussy was concerned. Oral sex can be so very pleasurable when it's done right."

"Do you think you can do to me what I did to your hand Timmy?" Rebecca asked. "Now that I've come once the second time will be easier."

"Sure auntie Becca." He said, getting into position between her thighs.

Instinctively he knew she didn't need any more warm up so he got right down to business. He was good.

"Ooh that's good Timmy, that's so good."

Timmy looked up at her smiling approving face from his place between her thighs even as he kept her erect clit pursed between his lips. Rebecca looked down at the boy and couldn't help but see his mother Suzanne's face reflected in her son's. It made her a little sad to think that she would never again experience the pleasures only Suzanne had known how to give her. Seeing Suzanne's son doing to her what her longtime friend and lover had done so well for so long balanced the sadness with some joy in the knowledge that she was helping to train the boy as his mom had asked.

Timmy was doing very well. He was a quick study and in addition to the moves she had demonstrated with his knuckle he threw in a few that were seemingly Suzanne's. It was almost like he was channelling her somehow. When, after a delicious period of tease and buildup, he took her clit between his lips and gently sucked while stroking her g spot with the pads of two probing fingers she came spectacularly. She was staring straight down at him when she did. Her hips and ass rising off the mattress and still maintaining contact with his mouth. Her hands grasping fistfuls of sheets, her eyes fixed on his, on hers, on the same eyes Suzanne's had looked back at her with when she had done her as well as her boy now was.

"You're a natural kid. Can't wait till my turn." Tonya said, breaking the spell after several moments of watching her friend in post orgasmic bliss.

"It will have to wait." Rebecca said after her breath caught up with her. "We don't want to confuse the boy. One lesson and one pussy at a time."

"Alright. He'll have to fingerbang me though while you suck on my titties. He's become very good at that with all the practice we've had at the shop. He can bring me off in under five minutes with such strong, firm, thick, fingers."

Timmy smiled at the compliment.

"Speaking of strong, firm, and thick, why don't you peel off those briefs and hop up here on the bed and lay back." Rebecca said. "Auntie Tonya and I have a special treat for you now that you have done so well on your first cunnilingus lesson."

Timmy wasted no time in doing just that. When he stripped off, his erection sprang back with a slapping sound against his abdomen reaching almost to his belly button.

Tonya grasped it and stroked it's base while Rebecca smeared the copious precum around the plum sized head.

"I'm still amazed by the size of this thing every time I see it even though that's been plenty of times by now." Tonya remarked.

"It is impressive, I'll grant you that." Rebecca agreed. "Not sure if I'll be able to work my way up to my specialty but it will be interesting to find out."

She then snaked out her tongue and ran it around the circumference of the mushroom shaped head.

"Ooh." Timmy moaned, as he hunched his hips in an effort to pop the head into auntie Becca's mouth. He failed as she had started licking up and down the length of the shaft instead.

"Relax and enjoy Timmy. Your aunties are going to lick and stroke you to a nice come. Full blowjobs to follow after you have passed a few more pussy eating hurdles." Tonya said before joining Rebecca in administering a tongue bath to the boys straining rod.

Timmy did relax and gaze down at the two foxy older ladies lovingly running their tongues from tip to root of his eager cock. Occasionally one or the other would kiss and lick the head and butterfly flicks of a tongue often teased at his frenulum although he wouldn't have known to call it that. It was just the sensitive spot on the underside of the shaft nearest the head as far as he was concerned. His aunties always paid close attention to it when the had been masturbating him and he was close to orgasm.

Tonya and Rebecca teased him and built him up for about twenty minutes until he seemed almost desperate. Then they relented and Tonya popped his head into her mouth and tongued his frenulum rapidly.

She was prepared when the first massive volley erupted so that she didn't gag and was able to swallow that and the several which followed. Rebecca jerked and stroked the boys cock to insure that they both milked every drop from his sack. Tonya kept the last mouthful in her mouth and then leaned over to share it with Rebecca. Each woman then took a turn kissing Timmy so that he could taste himself on their tongues.

******

On Monday Timmy was working as per usual at Tonya's garden shop. He was excited by the prospect of eating her out this evening. The plan was for her to drive him home so he could learn the best way to get her off orally in the big king sized bed in Rebecca's room. Tonya had never invited Timmy over to her place and she wasn't going to start now. She had a neighbor who was an occasional lover and didn't want to answer questions about what she was doing with a teenager in her house.

She had been carrying on her training of young Timmy in her office, sometimes after work and sometimes during lunch, and had supposed that this had gone unnoticed by everyone else who worked for her. Timmy had been introduced as the son of her late friend to whom she was giving a first job as well as mentoring. Everyone accepted this with one exception. Madison was a perky blond twenty two year old cashier who had taken an interest in the new guy. She had recently broken up with a boyfriend and had been scouting Timmy out as a potential replacement. He was a little bit younger but had potential she had thought to herself. What wasn't clear to her was the boss's actual relationship with him. Were they lovers? The way he looked at her sometimes made her think it possible. They often had lunch together in the locked office but that was possibly explained away by her 'mentoring' of him. After almost five weeks of his having worked there Madison decided to have a chat with her boss and gather some information.

"Hi Tonya. Do you have a minute?"

Tonya had encouraged all of the staff to be on a first name basis in her 'family' environment workplace so it was not discourteous of Madison to be familiar in this way.

"Sure Madison. What is It?"

"Maybe in private?" Madison pleaded.

"Sure. Come into the office. Betty is on the floor so you can leave the register for a bit."

Once inside Tonya closed the door behind them and motioned Madison to the chair in front of her desk.

"What's on your mind young lady?"

"Well, it's about Timmy."

"Has he been innapropriate with you?" Tonya asked, knowing he probably hadn't but playing for time to figure out where this was going.

"No. It's not that. Actually it's the opposite. I've been flirting with him a little and he doesn't seem to notice. I'm trying to figure out a way to get him to ask me out and I was a little afraid that I might be encroaching on your territory."

"What would ever make you think that?" Tonya said rather quickly, trying to tamp down any suspicions her young employee might have.

"I don't mean to imply you've done anything wrong and I don't mean to sound jealous although that's probably exactly how I sound. I guess it's just that he spends a lot of time alone with you and he looks at you in a certain way that makes me think he likes you like I'd want him to like me."

"I see where you might get that idea honey. We have spent a lot of private time together but you have to remember that he has lost both of his parents and his mother was one of my best friends. I promised to mentor him and I'm giving him some time to work through his grief."

"I do know that but he seems to have a bit of a crush on you."

Madison had also probably subliminally stored the memory of having seen what could have been Timmy's come decorating the side of her boss's hair when he had exited her office on his first day on the job. The satisfied look he bore and the glistening wet glob on Tonya's red hair added up to something Madison had considered and then dismissed as outlandish. Tonya had been surprised by the power of his ejaculation that first time and had failed to catch all of it in the washrag she had ready for that purpose. She had initially thought Madison might have caught onto something that day but hadn't had any vibe of follow up suspicion until today. No more mid day hand jobs or blow jobs she thought to herself. They would have to play it cooler.