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?"
