Training Tim Ch. 03: Final Exams

"She wanted to make sure we used protection against pregnancy."

"I have condoms."

"That's good, but I don't think we'll need them. I just finished my period so it's safe to come inside me if you'd like."

"Oh I'd like alright. I really don't like wearing the condoms."

That statement brought the question to Madison's mind about just when might Timmy have had occasion to learn about his dislike for condom wear. She didn't ask this question but instead said to him.

"I guess Rebecca is cool with us having sex in her apartment."

"Yeah. Rebecca is cool about sex. Tonya is pretty cool too. They both obviously know. They share a lot with me about what it was like for them when they were young like us."

'Is that all they are sharing with you?' Madison thought to herself.

*****

"What did you mean by that remark about being careful to Madison?" Tonya asked Rebecca when they had started on the road back to her place.

"The last time I saw her I had recommended they use protection against pregnancy."

"Sounds like good advice, maybe you should take it."

*****

Madison and Timmy wasted no time in getting naked in his bedroom. He had her lay back and then ate her out to a nice satisfying orgasm, fingering her special spot while he worked her pussy with his ever improving oral techniques. Then it was his turn to relax and have her service him. She spent fifteen or so minutes in full cock worship mode, lathering his length and girth with both saliva and compliments.

Finally she said. "As much as I'd like to finish you off with my mouth I just have to get this inside me, or as much as will fit anyway. I hope you don't mind."

"Of course not. I'm not sure we'll be able to get comfortable in this single bed though, maybe we should move this into the living room or Rebecca's room. She has a king sized bed."

How he knew what size bed Rebecca had was yet another question unasked but registering in Madison's mind. It was possible that there had been some innocent reason for him to know but that was becoming less likely as the questions piled up.

"Wherever you want. I just gotta have it and I gotta have it soon." Madison said as she planted a punctuating kiss on his cock head.

Timmy got up from his supine position and led the way back to Rebecca's bedroom. He found the wall light switch in the dark without any fumbling about and the bedstand light came on. Yet another question to add to the growing list but that could wait until Madison climbed aboard the thing she had dreamed about for weeks now. Timmy lay on his back once again and allowed Madison to dictate the pace and depth of her penetration. He held his cock up and watched her straddle his midsection and her hand join his in running his tip along the length of her well lubricated slit. She could see their reflection in the mirror above the bed and the scene was supremely sensual. Timmy played with her breasts and gazed into her eyes when she pushed herself onto him, gasping a sigh of delight as she did.

"Ooh, that is one big cock."

"And that is one tight pussy. You feel so good around me."

Madison leaned over him and they kissed while she raised and lowered her pussy onto his cock slowly and steadily. She slowed when she had taken in as much of him that she was likely to be able to. It was more than Tonya or Rebecca had been able to take in but he wasn't going to get all of it in without hurting her. Timmy reached between their joined groins with both hands and cupped her ass cheeks, one in each hand, to help support her up and down riding of him. Her thighs were losing some strength and were beginning to shake in preorgasmic excitement. Then she came. She bit into his lip and her thighs became almost spastic. It was good that Timmy had a grip on her ass so that she didn't drop down enough to injure herself. From Madison's perspective this orgasm was epic. Timmy held her in place and allowed her to ride the entire wave before he rolled her off of him and then lifted her to a doggy position facing the headboard.

He then took his time, enjoying a perfect view of her heart shaped ass set off by a coincidental tramp stamp of a heart with an arrow through it on her lower back. He was admiring both the tattoo and her beautiful ass as well as the way her pussy was expertly sucking his cock. Timmy could see Madison's face and reactions in the mirror. She was truly beautiful. He lasted almost twenty minutes and saw her through a couple of more orgasms until he could hold out no more.

The intensity of his orgasm and the hectic nature of their day to this point found him dozing off after a brief post coital cuddle. Madison, on the other hand, was energized from her orgasms and after laying with the now napping Timmy for a bit she wandered out into the living room to find something to watch on tv.

When she found the remote for the television and turned on the set, an on screen menu said that the input source was selected to an alternate external drive. There were options to change the input to one of several other inputs as well as a choice to play drive. She found the play button on the remote and pressed it.

*****

For the first few days of the next week at the garden shop Tonya noticed a change in the attitude of her cashier toward her. Tonya avoided having any alone time with Timmy until Thursday when the tension she was feeling made for an uncomfortable workplace. She asked him into the office to share lunch but kept the door ajar. She asked him a couple of direct questions and the answers he gave her caused her to flush a little at first but then, after regaining her composure, to ask Madison in to join them. With the office door now closed a conversation that was uncomfortable for all to begin started with Tonya acknowledging the obvious.

"I understand you saw our video. We were all planning to tell you about the situation and I think we all would have preferred you not find out the way you did but here we are."

Madison answered. "I would have rather not found out that way too, believe me. I was angry and jealous and then a little turned on all in a short time."

"I'm sorry honey. None of us would have wanted to make you angry or hurt."

"I told her everything auntie Tonya." Timmy said.

"Yes he did, including that he's been calling all you guys auntie. Kind of weird if you ask me but after I thought about it a bit kind of kinky."

"I'm glad it's out in the open." Timmy said.

Madison said. "When I first saw what was on the screen I couldn't believe it although I had so many suspicions. I went into the bedroom to confront Timmy but I saw him sleeping so innocently and I realized that we hadn't said we were exclusive, damn, we had really just started dating so I left him be and went back to the living room. I was still trying to figure out how to talk with him when he came out to the living room and saw what I was watching, for about the third time at this point, and with my hand in my panties."

"I saw her watching and was embarrassed until I saw that she was playing with herself. It got me hard."

"I know, and we put that hard to good use. We went back to the bedroom and I didn't leave till the morning. We didn't know when you guys might be back but I was ready to give a big fuck you to you both if you gave us any grief about having sex in Rebecca's bed."

"We had no plans to come back that night at all but we would have deserved the expletive if we had gotten it. Rebecca and I realize that Timmy's mother, despite being such a free spirit, would never have intended for her son to be merely a sexual plaything for her old friends."

'I don't mind being a sexual plaything.' Timmy almost said but instead opted for silence as the women continued.

"I got over it the past couple of days. Timmy told me that you were kind of training him in a way. I wasn't exactly a virgin myself so I have to factor that in. What I was having some trouble with was this whole awkwardness at work with you and all."

"I can see that." Tonya said. "Why don't we establish some new ground rules for around here then so as not to cause anyone embarrassment. Let's keep things on a professional basis during working hours. That means no more lunch time hand jobs or blow jobs for you young man, at least not from me."

"Don't look so disappointed Timmy." Madison said. "Maybe Tonya could let us stay late to lock up once in a while and we could revisit the employee break room,"

"I don't see why not. Just keep it safe and don't destroy any inventory with your rambunctiousness."

"I'm not disappointed." Timmy said. "I'm actually glad this is all out in the open because I hate lying even by omission."

"I know honey. No more lying. I think your auntie Becca will be glad this came to a head. She was feeling responsible for letting Madison know or at least letting you let Madison know. There was though, a part of her, frankly a part of all of us, that wanted this arrangement to continue. That's selfish I know."

"Oh I can understand wanting to be a bit selfish. He is a very good lover and anyone can see why you would want to keep experiencing him. I also get that I have all of you to thank for his developing skills."

"It was our pleasure dear."

"I had some pleasure too." Timmy said. This got a smile out of the two women and then Madison said.

"Maybe there is a way this can continue a bit. What I mean is that even though he was fairly gentle with me my pussy was pretty beat up for several days after our sex that day. Timmy has a very high libido, even for a teen, which was probably why he developed those masturbation injuries, and yes he told me about that and how all this started. His need for regular relief combined with that enormous cock makes me think that sharing the responsibility for taking care of it might work out for everyone's benefit."

"It will work out for my benefit, I can tell you that." Timmy said.

Madison punched him in the shoulder playfully and said to him. "Don't be so quick to agree and don't be such a piggie."

"Just kidding." He said.

"No you weren't." Tonya said. "You will be living the dream and who could begrudge you if you can get away with it. Enjoy while it lasts."

"I hope it lasts." Timmy said, and then to Madison. "I hope we last too."

"We might." She said. "if I get beyond thinking of you as my sexual plaything." Madison then added a playful grope of his groin for added emphasis.

"Now now you two. I thought we had agreed on professionalism in the workplace."

"You're right Tonya." Madison said. "Work at work, play at play."

"To continue with our new honesty policy I wanted to let you know something about our plans for this weekend." Tonya said. "I was planning to train Timmy in the fine points of anal sex. Rebecca and I wanted to surprise him with this treat but you may as well know now so that you can raise any objection you might have."

"Anal sex?" Timmy asked.

"Yes. You heard correctly. Madison, you can come and watch if you like or you can think about it and let me know later if you either prefer to be present or if you'd rather it not happen at all. I know it's a lot to absorb all at once."

Without hesitation Madison replied. "Heck yes I want to be there. I can't believe you could even consider having him back there. I want to see that in person in order to believe it. I couldn't imagine him in my back door. I would be scared shitless."

Then the two women laughed at that last remark and the meeting broke up with Timmy leaving first and smiling broadly.

*****

Saturday night was the night assigned for what the women wanted to call Timmy's final exam. Doris, who was the least sexually experienced of the three aunties despite being the oldest, had surfed the internet to see if what Tonya had in mind was even possible. The nurse in her was afraid of injury. Tonya had told her to try a few keywords like massive, anal, gape, and BBC. Doris found quite a few examples of women smaller than Tonya taking in cocks the size of Timmy's so she was satisfied that it was safe and was also curious, as Madison was, to see it in person. Rebecca had seen her friend do it before and so had no lack of confidence about Tonya's ability.

Tonya had told Rebecca Thursday night after her talk with Madison and Timmy that the young lady had seen their escapades on the thumb drive and that she had taken it well all things considered. Rebecca had, as Tonya had predicted, been relieved that she didn't have to initiate that awkward conversation. She was a bit surprised that the young lady expressed eagerness to witness her boyfriend break his anal virginity with a woman twice his age and her boss to boot. She wasn't surprised that Timmy was ok with her being present. He had become accustomed to performing before an audience.

Doris was told about Madison being in on their secret Friday night. The widow had planned to be with them on Saturday for the anal cherry popping to satisfy her own curiosity. The others thought it fair to let her know that the young lady had seen the video of her squirting all over her boyfriend's cock and wanted to give her an out in case that would be too embarrassing for her. Curiosity overcame modesty and she was with Rebecca when Madison and Timmy arrived at the apartment from their afternoon out and about.

"Hello Madison, its nice to meet you." Doris said.

Madison took the hand Doris had extended to her when she had stood and approached the young woman.

"It's nice to meet you too."

There was some awkward silence for a time after Timmy and Madison had taken seats, a silence which Rebecca finally broke.

"Look everybody, this is not a conventional situation. We all know that. Madison has seen us all with our hair down so to speak and now we are all going to be in the same room where it's likely to get pretty intense. I hope it can be relaxing enough for Timmy to get out of it what he needs to finish his education."

"Education?" Doris said. "By this time he could be teaching the class."

Doris said to Madison. "I know you saw me having sex with Timmy on that recording and that was a little embarrassing to me at first and I'm pretty sure by now that you realize it was me who passed you guys making out in the car after your first date and that is probably embarrassing to you."

"I thought that was you. You're a nurse aren't you?"

"Yes I am. That has helped me a lot in familiarity and openness with the human body but emotions and such can be more complicated. I think I would be jealous and angry if three older women had been taking advantage of a boy I was interested in."

"I was a little at first but I've worked it out. I'm not angry with any of you."

"And I don't feel like I'm being taken advantage of." Timmy chimed in with.

"Anyone for a drink?" Rebecca said. "I think it will help us relax and make the evening go smoother. I've got some wine chilling in the fridge."

The three women indulged in several glasses of wine each before Tonya finally arrived. Timmy had none because as his auntie Becca kiddingly pointed out he was the only one not twenty one yet. It was also due to the fact that his Mormon upbringing had put alcohol off limits and Rebecca wanted to leave some areas of his character unsullied. It was bad enough, she had thought, that they were turning him into a veritable satyr.

"What kept you Tonya?" Rebecca asked.

"I had to visit three different sex shops to find the right butt plug and then I've had to have it in for a few hours. Is that wine? I could use a glass or two."

"Sure is. Let me get you some." Doris offered, already feeling more relaxed from its effects.

The women spent another hour drinking and chatting and avoiding for the time the subject of the elephant or elephant cock in the room. Madison was sitting beside Timmy and stroking his leg and then noticing his having shifted to rearrange his uncomfortable bulge, unzipped him and stroked him slowly in plain view. The trio of cougars threw an appreciative glace at both his erection and her boldness in fondling it in front of them.

"Tell me again how you prepared." Doris asked Tonya.

"This goes back to my days from the swing scene. I've seen anal done without the right prep and it is anything but erotic unless scat is your thing and it's not mine."

"Scat?" Timmy asked.

"Never mind dear. Tonya is a pro and we are not going there. Think of what is normally in one's ass and then imagine that coating your dick." Rebecca said.

Timmy shuddered and his dick softened momentarily until Madison gave it a kiss and a lick.

"Prep is the key. I've been on a liquid diet for two days and I gave myself a couple of enemas this morning. Squeaky clean back there now. Then I lubed up and put the one butt plug I had laying around in to stretch myself out a bit. I realized I needed more stretching so that was where the delay in getting here came in. Finding the right tool for the right job."

"I think Madison has the right tool in hand right now." Rebecca said. "Why don't we take this show to the bedroom?"

"I thought you'd never ask." Timmy said and then eagerly led the way.

*****

Rebecca and Tonya got naked immediately and started making out with each other on the bed. The purpose was to get Tonya on edge for her hoped for anally induced orgasms. Madison was impressed with the shape the duo were in for being forty two and thirty nine respectively. It gave her inspiration for maintaining herself in the years to come. She was given the task, which she willingly accepted, of recording the sexcapades for their later viewing pleasure. She zoomed in on Rebecca and Tonya's expert cunnilingus techniques. Madison had never experienced lesbian sex but if it was anywhere near as fun as these two made it seem she might try.

Doris was intent on keeping Timmy hard with her hand and an occasional suck. She also kept a hand under her skirt as she was quite horny. This would have been the night for her turn at Timmy's pussy pounding but for the anal initiation and she found herself yearning for it.

Tonya and Rebecca got each other off once orally. Rebecca then pulled the butt plug out from Tonya and gave it a playful lick which Madison caught perfectly including Rebecca's wink for the camera.

"Look at that gape Timmy. That's for you and it's very well lubricated. Cherry flavored, yummy." Rebecca said. "It looks like Doris has been keeping you nice and hard. Now we need to lubricate that dipstick of yours. No need for a condom. You can't knock someone up dumping a load in their back door."

"Are you going to rub some of that lube on me then?" Timmy asked.

"No. I think saliva will do. Madison, do you mind giving me a hand? There's a lot of surface area to cover here. Give Doris the camera so we can continue this little sex documentary."

Doris recorded Madison and Rebecca running their tongues up and down Timmy's length and coating it with their spittle. Tonya had assumed a doggie position and was observing through the reflection in the mirror over the headboard the double tongue bath the big dick was receiving. Madison's tongue made contact with Rebecca's a time or two while they were working Timmy and the older woman was pleased to find that the sexy twenty two year old did not recoil.

"That's a good start but I think it could do with a good coating of vaginal juices. Would you care to oblige Doris."

Doris answered by handing the camera back to Madison and bending over the foot of the bed. She pulled her skirt up over her waist and pulled her sopping panties to the side. Timmy took the offer and plunged in. Since he was already slickened up he sank to the root in one stroke. He knew that Doris needed to come so he did her quickly, banging her hard and fast, just the way she liked after she was fully aroused and was she ever aroused. In about twenty strokes with his balls banging against her clit she came with a flood of her juices spraying around his cock. Madison captured it all and then followed her boyfriend's cock as it went from the widow's pussy to her boss's winking asshole. Timmy's tip popped through the sphincter without a struggle due to the stretching administered by the butt plug. He pushed and withdrew in one or two inch advancements while holding her cheeks apart until his pubes were tickling her crack and he was fully embedded.