Training Tim Ch. 03: Final Exams

This is the third installment of a series. It would be best understood if the previous two installments were to be read first but hopefully it can stand alone. Character development and background will not be repeated in detail. All characters are over the age of eighteen when any sex takes place.

*****

Timmy lay back on the king sized bed once shared by his mother and the woman now deep throating his thick cock. He luxuriated in the sensation and could feel the beginning tingle in his balls that preceded an impending orgasm. It would be a big one.

It had built up over the course of more than an hour of cunnilingus he had engaged in with Doris from next door. He had brought the fifty six year old to multiple orgasms and as a reward she had sucked his cock as best she could. His size prevented her from doing a top notch job so she opted to bring him back to auntie Becca who was by far the most accomplished fellatrix of the three older women overseeing young Timmys sexual training.

Doris played with the hairs on his chest and said to him lovingly. "You were wonderful dear. I know I was a tough nut to crack but you got the code eventually. I never came so much in my life and that's saying a lot."

"You did come a lot. I'm glad you enjoyed it."

"And you have become quite the gentleman. Ladies first, just like we taught you."

Doris then tickled and fondled the teenagers balls while the forty two year old Rebecca did the incredible. It never ceased to amaze Doris or anyone else who witnessed the act how easily and well Rebecca was able to inhale even the biggest of cocks. Her head bobbed up and down taking the boys massive meat to the root with each pass. Her throat would bulge slightly as it was filled but there was no gag reaction. Rebecca was very proud of that fact. She was a true virtuoso of cocksucking and had been one going all the way back to her days on the swinging scene. Timmy's mother, the late Suzanne, had been amazed, jealous, and proud of her long time friend and lover all at the same time. It would have pleased her to see her son's boner disappearing again and again into her friend's gullet.

Rebecca pulled her head off the saliva coated cock to say. "You can come now young man. Let's not be greedy. Fill my mouth with that hot load."

"Let me help things along a bit dear." Doris said as she applied some lube to her fingers. She had been fondling and tickling Timmy's balls but was now going to give him her never fail prostate massage. He still clenched a little as she entered him but it was much easier than the first few times she had shown him this little trick.

Doris was a seasoned RN and knew all of the hot spots on the human body and Timmy had thoroughly enjoyed his milkings from his auntie Doris when she threw in this wrinkle. Two or three pumps from her fingers in his ass was all it took for Timmy to send his seed into Rebecca's sucking mouth.

"Yummy as always." Rebecca said. "You have the sweetest come Timmy. I'm so glad you like all the pineapples and other fresh fruit we buy."

"I'll eat whatever you want me to auntie Becca as long as you keep sucking my dick like that. Now what do I have to eat to finally get to fuck you?"

"Yes." Doris said. "When does he get to fuck us? I think the poor boy has been put off long enough."

"I suppose you're right. Tonya has said the same thing. I think I'm the one dragging my feet and it's on account of the size of that thing." Rebecca said to Doris after Timmy had wandered off down to the bathroom. "I'm a little afraid it will hurt me. From my days on the swing scene you would think that I had learned to accomodate even the biggest cocks but I have a somewhat shallow pussy. Thats probably why I learned to compensate by becoming a deep throat expert."

"You certainly are that honey. I could never do what you do."

"What about you Doris? Aren't you afraid that monster cock is going to beat up your pussy."

"Not at all dear. I had a full hysterectomy after my younger son was born. There is no cervix to bump into so that big boy can bottom out inside my kitty cat."

"Didn't that affect your sex drive?"

"No, my ovaries and hormones remain intact. I lost some of my sex drive after menopause but seeing and touching and tasting that boys meat has turned me into a senior carnivore."

"Maybe you should be the first to take him inside you then."

"As much as I'd love to, and believe me I've thought of little else for the past seven weeks, it really is your place to take his virginity. He will be gentle with you. I can be in the room with you guys if that would help."

"That's a kind offer Doris. Let me think about it. Let's change the subject now, he's coming out of the bathroom."

"Do I get to learn about fucking soon?" Timmy said to both of his special aunties when he got near them.

"Probably soon." Rebecca said. "Let me talk with auntie Tonya first and let's all get on the same page."

******

"It's beyond time girlfriend. That boy has been fuck ready for over a week." Tonya said when Rebecca stopped by the garden shop the next day.

"Where is he now?" Rebecca asked.

"I think he went to lunch with Madison. I told you about her."

"And you let him go out with her? He's not ready yet."

"You mean you're not ready for him to be ready. What would Suzanne want? He's her son after all, not your, or our, personal boy toy as much as we might want him to be. He needs to spread his wings. We need to show him how to safely use what he's packing or there will be a lot of collateral damage in wrecked pussies starting with my cashier."

"Well I suppose I wouldn't want to be responsible for that. I figure tonight is the night. Doris is willing to stand by in case I need a tap out."

"Look at you. I can't believe you are scared of Suzanne's little Timmy."

"Not scared really. Just being prudent. What about you? I'm pretty sure you won't be able to fit him all in."

"Not through the front door anyway."

"You wouldn't, Tonya."

"Why not? He deserves a full education."

"He might blow you out back there honey. I know you've had a lot of cock up your back door but this would be a stretch, literally."

"Why don't we cross that sphincter when we get to it. You need to worry about yourself. How to pop his cherry and make it memorable for him while protecting that pussy for future loving."

"Enough for now. I see them coming. I'll let you know how it goes tonight."

"I can't wait to hear." Tonya said, and then to Timmy and Madison who had just approached. "How was your lunch?"

"It was great Tonya. Madison knows an all you can eat seafood place and we really had a feast."

"Timmy can really eat when it's good." Madison said.

'You don't know the half of it' Rebecca thought to herself.

"He does have quite the appetite. I can attest to that." Tonya said and Timmy blushed.

"Now back to work both of you. I have a business to run here."

"I guess we are racing the clock if we want to finish his training before he is set loose to wreak havoc with that deadly weapon." Rebecca said.

"Let me offer you a tip sister, although you probably don't need to be told this. Take him from on top the first time. That way you can control the depth of his penetration a little better."

"I was thinking the same thing. No after work blowjob for him now Tonya. I want him able to pop without fucking for forever."

"Ok, I promise. Good luck tonight."

******

This was to be the night, Timmy had been told by Tonya before he left for home on the bus. She explained that there would be no after work blowjob because auntie Becca wanted all his cum for herself.

It had been a very eventful two months for the teen. The death of his father followed by having to leave his cloistered environment in Idaho and land in the bay area would have been jarring enough for anyone. To discover his mother, whom he had not seen in many years, was on death's door was shock number two. Then he had been taken under the wings of not one, not two, but three older women who had made it their mission to educate him sexually.

They had taught him how to masturbate safely. It amazed him now to think that he had once stimulated himself in such an unorthodox and vigorous way that he had caused himself injury. They had taught him to masturbate each of them and they had each brought different ways to manually delight him into their play. They had taught him how to use his mouth and lips and tongue on them to bring them to orgasm. Of course, last but not least, they had blown him. He was too young and inexperienced to have heard the expression that there is no such thing as a bad blowjob but he had been privileged to have had some of the best, especially auntie Becca's blowjobs.

It still felt weird to him to be calling these three older women auntie as they were all unrelated to each other and unrelated to him but since the precedent had been established so be it.

Rebecca was decked out in the sexiest outfit she owned. She didn't need to seduce Timmy by this time but wanted to make the visual memorable for him. To that end she had also set up a couple of video cameras to memorialize the event for all. She had on a red lacy negligee, silk stockings, and was wearing no panties. She was also wearing her seldom broken out, four inch high heeled fuck me pumps. She had put on perfume and makeup including some glossy smear proof red lipstick.

Tonight she wanted to be a centerfold, a porn star, an escort, a fantasy woman for her special protege's first fuck.

"Wow auntie Becca. You look so hot."

"That's the idea Timmy. Why don't you join me in my room after you take a shower. I'll be waiting."

She then kissed him and felt his eyes following her sexy strut back to the bedroom.

Less than five minutes later an eager teen, still toweling his head dry, was standing naked at the foot of the bed and admiring his auntie in her special attire. His cock was swollen with anticipation.

Rebecca crooked a finger and bade him join her in the bed. He climbed up and tried to cover her body with his.

"Easy big boy. We are going to do this my way and you will love it."

She rolled him off of her and took his cock in her hand, stroking it gently.

"Do you like my outfit?"

"Oh yeah. I've never seen you dressed like this auntie Becca."

"Well I'm glad. I wore it special for you. You can touch it if you want, touch me through it. Touch my stockings. Run your hands over them and stroke my legs."

"That feels so soft auntie Becca. You feel so soft."

"It does, doesn't It? Would you like to take your cock and stroke it on the stockings? That would feel good too."

"Could I? Wouldn't that stain them?"

"It might, but that's ok. Go ahead, run that fat cock of yours along my stockings."

Timmy got in position over her and ran his cock up and down each silky leg from one end to the other. He did this to each leg several times, leaving trails of precum in his wake. Rebecca toyed with her clit and worked a couple of fingers inside herself to prepare for his penetration.

"Lay on your back young man. Are you ready to get that cock into your first pussy?"

"Am I ever?" Timmy answered.

Rebecca straddled his waist and took his cock in hand, guiding the tip to her entrance. She took a remote control she had on the bed and turned on the television monitor above her dresser. One of the cameras, the one at the foot of the bed, had a perfect close up view of young Timmy's cock poised to penetrate his aunties pussy and become virgin no more. This cameras feed was displayed on the monitor and Rebecca brought his attention to it.

"Look how big your dick looks on that screen Timmy. My little pussy is going to have to work very hard to suck that monster inside but here goes."

"Oooh." Timmy moaned in pleasure as her labia first pressed against and then splayed around the head of his cock. On the monitor he could see Rebecca's perfectly formed ass and the back view of her pussy lips tenderly kissing his cock head. She dropped down then and enveloped that head with a gasp of her own.

"Aaahh. That is one nice cock Timmy."

Rebecca slid down another couple of inches and then back up and Timmy could see her juices coating the top third of his cock as she slowly fucked him. Rebecca looked back over her shoulder at the monitor to enjoy the nice view of this cherry picking.

"Look how my cream is coating your cock Timmy. Can you feel how snug and warm and wet it is?"

"Yesss. Yes I can auntie Becca. It's so tight."

"Better than my mouth?"

Timmy was speechless watching more and more of his cock become slick with Rebecca's juices. She was slowly riding the boy, taking him deeper with each pass until his tip hit her cervix with several inches of cock meat still outside of her clutching cunt.

"Ooooh yeah." Timmy moaned.

Rebecca continued her slow milking of his throbbing rod and said. "I'll take that as a yes to better than my mouth or at least different. My pussy is sucking that cock with each stroke, no gagging and no teeth."

"It feels wonderful auntie Becca. I won't be able to last long this way."

"Good. I don't want you to. I want you to enjoy the feeling of my pussy walls gripping you and milking you. I want to feel you spray that hot load inside me. You let me know when you're ready. Stroke my stockings big boy. Cup my ass in your hands but don't pull me down. You're bottoming out as it is."

"Getting closer. I can't hold it anymore. You better get off if you don't want to get pregnant."

"No worries there Timmy. Fill me. Fuck me. Shoot for me."

With that said Rebecca leaned over and kissed the boy. Their tongues dueled as his cock head swelled and then spurted volleys of scalding cum deep into her pussy.

She waited a couple of beats until he started to shrink and then rolled over onto her back next to him. The foot of the bed camera caught his excess cream oozing from her slit and down the crack of her ass.

"That was wonderful Timmy. Did you enjoy It?"

"I sure did auntie Becca. Did You? Did you come?"

"I didn't Timmy but that doesn't matter. I'm going to come when you fuck me again in a little while."

"Am I going to get to fuck you again tonight?"

"Yes you will. That is if you'd like to do me again."

"Well of course I want to."

"Good, now let me clean that big boy up for you."

Rebecca set about licking and sucking their combined juices off of his semi flaccid cock. She then replayed the video of their first fuck session fo them to watch.

"See the way you stretch me out? You have a very big cock and when we go again I'm going to let you be on top. You have to go slow and only put in about two thirds of that log before you withdraw for the next stroke. Do you think you can do that Timmy?"

"I think I can auntie Becca."

"I'm probably going to keep a hand on you hip to remind you to be gentle and not go too deep. I may be diddling my clit with the other hand but then again I may not have to. You have a nice little upcurve to that cock and it should rub against my special spot in the most delicious way, just like we taught you how to use your fingers on us. You will be using that cock tip like some very fat fingers on my insides."

Rebecca clicked over to some other porn she had cued up to play and she showed Timmy some excellent cocksmanship techniques from the pros. She was manipulating his dick back to readiness and when he was sufficiently hard she said.

"Are you ready to saddle up young man? Ready to put that specimen to good use again, to fuck me and fill me with more of that spunk?"

"I sure am auntie Becca." Timmy said, getting between her nylon covered legs and placing his tip at her entrance which was still oozing his previous load.

He pressed forward and their combined juices, still simmering in her box, lubricated his entrance and progress to about half his length on the first slow thrust.

"Oooh." They both gasped simultaneously at the pleasure this contact provided.

Now it was Rebecca who was able to enjoy the view of the toned and bare eighteen year old ass rising and falling on the monitor as he pumped her full of cock. She had been filled with many many yards of cock over the years but his was special. This was the son of her late lover and friend. Suzanne had usually been the top when they had engaged in any strap on play and looking up into Timmy's face which so resembled his mother's, Rebecca could imagine her still alive and loving on her.

At first she had kept a hand encircled around the base of his penis so he would have an idea about how far he should penetrate her without causing her pain. Timmy quickly caught on and he also made an effort to maximize contact with her upper pussy wall, tantalizing her g spot in the process. He certainly was a quick study Rebecca thought to herself. She released his cock and let him work it, massaging and stretching her insides.

"That's so good. Do you like how it feels Timmy?"

"Oh yeah. Your pussy feels so tight auntie Becca."

"I'm afraid it won't be quite so tight when you're done with it but keep fucking me. It will snap back. It always has."

Rebecca was able to play with her clit and her nipples while Timmy stroked his cock slowly and steadily in and out of her hungry kitty. She orgasmed twice and Timmy was very pleased by this.

"This is so good. You are such a good boy. Let me flip over now. I want you to do me from behind."

Timmy withdrew and Rebecca flipped on her stomach and lay flat. She also reversed position on the bed so that the foot of the bed camera was focussed on her facial expressions when Timmy got into position and tried to reenter her.

"No baby, careful there, that's the wrong hole. Try a little lower."

Timmy angled his cock a little lower and found the correct entrance.

"Ok, now push slowly all the way in." The natural swell of her buttocks cushioned his advance and only allowed penetration she could accommodate. 'That was a close one.' She had thought to herself when she had felt him probing her anus. She had engaged in anal sex many times over the years but never with meat that thick and never unlubed.

"Ok baby. Pump away. You can go faster as you get closer."

Timmy fucked away with his balls bouncing against Rebecca's ass with each stroke. She had a hand buried in her crotch furiously working her clit to orgasm after orgasm.

"I'm going to come again auntie Becca." He gasped.

"Do it. Do it." Rebecca said and she reached around behind his ass to pull him in tight while he emptied himself into her. She kept him tied to her as a bitch in heat might be tied and she felt his weight rest on her back in exhausted pleasure. The throbbing and pulsing inside her was heaven.

When he had rolled off of her she rolled back on top of him face to face and kissed him.

"I'm so glad I was your first. It made me feel close to your mom again. You are going to be a wonderful lover."

"Do you really think so?"

"I know so. Madison and every girl after her is going to have a wonderful time with you."

Timmy reddened a little and said. "How do you know about Madison? We're just friends you know."

"It's ok baby. Your auntie Tonya told me. Don't worry. We're not jealous. As far as being just friends, why nonsense. She is very interested in you. She might be jealous or misunderstand though, so you probably want to keep the nature of the special relationship you have with your aunties on the down low for now."

"Ok, I will. We have a movie date tomorrow after work. I'm excited about that."

"Good, you should be. Let her seduce you a little if she wants but don't get too carried away. Your auntie Tonya is anticipating a nice session with you the night after tomorrow. There are many things you can learn from her and auntie Doris."