Training Tim Ch. 03: Final Exams

Everyone then, was in on the plan with the exception of Madison who had a plan of her own for when the delivery was complete. She and Timmy had flirted, held hands, and even snuck the occasional kiss in the days since their movie date but Madison was very eager to do more.

Tonya and the rest of the employees left at six, which was closing time. The delivery was made just after that and Madison could have started driving Timmy home before seven but instead coaxed him back to the break room to pick up where they had left off outside his building.

"Kiss me. I'm dying to be held." She said to him after closing the door to the break room behind them. This was unnecessary as the shop door was locked and they were alone but Madison was taking no chances.

Timmy pulled her close and gave her a full body hug while kissing her deeply and passionately. "You feel so nice." He said to her. "You smell great too. What are you wearing?"

"Soap silly. That's about it."

"I like your soap. I like the way you kiss too."

Timmy then cupped her ass in his hands and drew her in for another deep kiss. She felt him against her abdomen and reached down to explore his size.

"Oh my! Aren't you excited." She said, taking a step back to admire his bulge.

"You make me excited. I like kissing you. I liked kissing your breasts the other night. I'd like to kiss you all over."

"Sounds wonderful." Madison said while unbuttoning her blouse.

While they were seated on the sofa and kissing, Timmy fondled her breasts and undid her jeans as in the car. Madison unzipped his pants and worked at fishing out his erection with little success. He stood before her to make it easier and when she peeled down his shorts her mouth flew open in amazement at the size of the penis bobbing in front of her face.

"Oh my God!" She exclaimed somewhat fearfully. "That is the biggest cock I've ever seen."

"I'm sorry. Is it too big?"

"Don't be sorry. I'm just surprised that's all." She said, taking hold of it with one hand and stroking it.

"That feels good." Timmy said.

"This should feel better then." She said as she planted her lips on the tip and snaked out her tongue. "May I suck it, or at least try? It looks delicious."

Timmy didn't answer but didn't object either when she stretched her mouth around his tip and began to swirl her tongue. He took her hand which was still around his shaft and showed her how much pressure he liked when he was being stroked. He was glad she didn't ask if he had ever had his cock sucked before because he didn't want to lie and couldn't tell her just yet that Rebecca and Tonya had been blowing him regularly. He was able to tell her that she looked beautiful and that she was making him feel wonderful.

"Why thank you sir." Madison said before getting to work again tonguing and stroking his shaft and balls.

Timmy gazed down upon her beautiful face and breasts and his day long unspent load began to bubble up. "If you keep that up Madison, I'm going to come."

"Good. I want you to. Come wherever you want. In my mouth, on my tits, on my face, wherever you want. Just come for me. I want to make you happy."

Making him happy was what she was doing. Madison was nowhere as accomplished a cocksucker as Rebecca and Tonya were but she had been around a number of cocks in her young life and she was most definitely a pleaser. Her striking good looks added to his excitement and within five minutes he could restrain himself no more. His aunties had been right to edge him. He would have a nice tribute for Madison's efforts to offer.

"I'm going to come and it's going to be a big one." Timmy was trained by his aunties to give warning so as not to shock or surprise a lady. Nevertheless the volume of the initial blast overwhelmed Madison enough that her head backed off and the next two streams splashed the side of her face and dribbled onto her open blouse. She then regained enough composure to surround the pulsing head with her lips and swallow the rest.

Smacking her lips, she scooped the come from the side of her face and fed it to herself.

"Wow! You weren't kidding. You did come a lot. Tastes good too."

ln response Timmy pulled her up to her feet and kissed her again so that they could share his essence, still on her tongue.

"That's hot!" She said.

"Can I kiss you now?"

"I thought we were just kissing silly."

"No, I mean down there. Can I lick you? Kiss your pussy?"

"I'd love that." Madison said and then she peeled off her jeans and panties revealing a neatly trimmed blond haired pussy. She lay back on the sofa and Timmy got down between her legs and inhaled her arousal.

"Oooh yes. I like that." She said when his tongue and lips began to tease and lick her outer lips and he puffed warm air onto her straining clit. Timmy licked and teased his way around her pussy for a good twenty minutes, discovering what she liked and bringing her close to orgasm several times before backing away to a new erogenous area.

Finally in frustration she took hold of his head by the hair and pulled him to her clit where he obliged with a rapid tongue flicking of the engorged button. She came and then after he spent some time licking her inner lips he returned to the clit, this time sucking and licking simultaneously so that she came again.

"That was so good. I could lay here and have you do that for hours but we better get you home or that woman you live with might tell Tonya you were late getting back. I don't want her to think I was taking advantage of you."

"Oh, if you mean Rebecca, she's cool. I think she likes you. Tonya says good things about you too."

"Let's get you home then so that they continue to think well of me." Madison said while getting dressed.

*****

Rebecca was dressed in her bathrobe with nothing underneath and seated watching television when Timmy opened the front door.

"I'm home Rebecca, and Madison is with me." Timmy announced and warned.

"You're a little late. I was getting worried." Rebecca white lied. "Oh hello Madison. It's good to see you. Please forgive my appearance. I just got out of the shower."

To Madison Rebecca looked nothing like a woman having just showered for bed but more like a woman dolled up for her young lover's return home. She had her makeup and lipstick on and before she pulled the top of the robe tighter was showing some cleavage.

"No problem Rebecca. I volunteered to take Timmy home after work. We had to stay a little late to accept a delivery for the shop."

"Tonya asked me to stay. I guess I should have called." Timmy said.

"It's ok Timmy. On account of my promise to your mom I guess I'm acting the part of an overprotective mother." Rebecca then said to Madison. "Would you like to come in for a few minutes? Could I offer you something to drink?"

"No thank you. I should really be getting home. My folks will be the next ones worried even though I'm over twenty one."

"That's right. You still live with your parents. That must make dating difficult for a vibrant young woman such as yourself. Perhaps I can make myself scarce some evening so you two can have some privacy, provided of course you use protection."

Madison reddened with embarrassment partly from Rebecca's noting of her still living at home circumstance and partly from the older woman's openness about sexuality. She thought to herself which was It? Was Rebecca merely a friend of Timmy's late mother looking after her young charge or were the two of them involved sexually? Madison couldn't be sure but was picking up a variety of conflicting vibes. At the very least Rebecca seemed cool with Timmy and her having a full dating relationship and she supposed that the less questions asked the better.

"We'll be careful Rebecca." Madison settled on as a farewell while the older woman stood with her in the foyer.

Rebecca took her by the shoulders and leaned in to kiss her on the cheek. Rebecca inhaled a familiar aroma and then pointed out the stain on Madison's blouse collar.

"You might want to soak that when you get home. You must have dripped some mayonnaise from a sandwich or something."

Rebecca winked at her and Madison reddened again before mumbling "Thanks, I will."

"She's such a pretty girl." Rebecca said to Timmy after Madison had left. Rebecca then dropped her robe to the floor and displaying her naked body before the teen and asked him. "Have you got any more of that mayonnaise left to fill my box with?"

"I sure do auntie Becca. I sure do."

*****

Sunday was the day Doris was finally going to experience what she had been longing for. She was reluctant at first to have Rebecca record the session but masturbating with her big John dildo the past few days while viewing the shared recordings of Timmy doing both Tonya and Rebecca convinced her that fair was fair and that she might enjoy reliving the memory when this young man grew tired of older pussies. She hoped that wouldn't happen anytime soon and she wanted to make this experience one worth repeating for the teenager.

Doris had bathed and perfumed her body in anticipation. Looking into the mirror of her bedroom dresser she assessed her fifty six year old body and in the lighting which she had dimmed for the occasion she liked what she saw. Her sexy sheer nightie had been on ice since well before her husband's death but she had not let herself go and other than normal aging she would put her body up against any woman's. There was some extra padding around the hips and butt as might be expected but her large breasts were not as saggy as those of her contemporaries were. All in all she was a very acceptable looking GILF as she had recently come to understand what that acronym stood for.

Rebecca was at the ready to record when she looked around the bedroom she had never been in. She and Suzanne had both been over to her neighbors place a few times in the previous years but never in this sort of circumstance. She noted a picture of the widow's late husband Frank as well as one of each of their two sons. The pictures of the sons was from a time when they were in their teens and Rebecca thought it a strange juxtaposition. The two boys gazing down upon their mother, who was dressed to be fucked and looking lustfully at the naked teen at the foot of her bed stroking his dick to ready it for just that mission. Rebecca could imagine them waiting their turn but knew that such wanton behaviour would never be her neighbor's way.

Doris was flowing freely. She had placed towels on the bedspread because as she had confessed to Rebecca she had been a bit of a squirter back in the day. She had prepped herself some with big John and was giddy with anticipation for even bigger Timmy.

"Are you ready Doris?" Rebecca asked.

"Are you kidding? I've been ready for weeks now."

"Well then why don't you ask for It? Ask him then, I think he's ready too, aren't you Timmy?"

"I am ready." Timmy said from his new position on the bed between the thighs of a woman old enough to be his grandmother. He was now stroking his cock with the tip inches from Doris's yearning entrance. He was so close Doris could force contact if she slid toward him even an an inch but she resisted and played along with Rebecca's game.

"Please put it in me Timmy."

"Come on now Doris. Loosen up a little. We're all friends here. How about a little Fuck me with that big dick of yours or something like that. Remember, we are going to be watching this later after Timmy has moved on and I want it to be as hot as possible. Reach back and channel your inner slut like I know you can."

Doris was now grateful that Rebecca was here with them and playing director for a dirty movie that she was to be starring in. Otherwise the filthy language that next emanated from her proper mouth would have never escaped.

"Are you going to keep wanking that thing or put it to use Timmy. Why don't you sink it deep into my pussy."

Timmy penetrated her with his tip and sank only a few inches in, teasing her and himself at the same time. "Like this auntie Doris?"

"No like this?" Doris said reaching around to grab his ass and pull him all the way in.

Timmy felt his balls nestle in the crack of her big bubble butt and felt his cock finally experience full immersion in warm pussy from tip to root and it was a fabulous feeling indeed for the young man.

"Now fuck me damn it! Pound that pussy and make it yours. It feels so damn good inside me, stretching me out."

Timmy began a slow in and out with which Doris quickly grew impatient with and found herself gripping his hips to quicken the pace. "Ooh yeah. That's better baby. Pound it. Pound that pussy."

Rebecca zoomed in on the way her lips clung to his cock with each stroke and even caught the slight tummy bulge created when he was fully inside. Rebecca found herself feeling slightly jealous of Doris being able to experience Timmy's pubes banging against her clit again and again as he slammed into her. There were certainly advantages in having no uterus she thought, although she was grateful she still had hers.

She reached out and played with Doris's boobs while the older woman was being serviced so skillfully. Under other circumstances the widow would have recoiled from any female to female contact but she was lost in the moment. Rebecca sensed her approaching orgasm by the intense look on her face. She looked so proper in one sense, her perfectly coiffed hairdo set off by it's flecks of grey, and so primally lustful in another like a savage rapacious cougar. Rebecca leaned in toward Timmy and told him to pull out when she gave the word. At the moment of Doris's climax she pushed Timmy backward and his dick emerged, creating a sucking sound followed by a massive stream of squirt that blasted against his abdomen. He instinctively took his cock head and strummed it up and down Doris's spasming slit and spanked her clit with it through several more squirts.

"We might need more towels honey." Doris finally managed to say when her breath caught up with her. "Why don't you flip me over now and drive that python into me from behind. Fuck me doggy baby like the animal I am."

"Why Doris. I never knew you had that kind of language in you." Rebecca said.

Rebecca then got an excellent shot of Timmy penetrating Doris from behind and plunging into her again and again. His balls bounced against her clit and he started to spank her fleshy buttocks in time with his thrusts.

Rebecca caught the action in profile which served to highlight the prodigious amount of meat Doris was engulfing with her pussy. The photos of her boys were also visible in the background from this angle as they seemed to be silent witnesses to the ravishing of their mom.

"Does that feel good Timmy?" Rebecca asked.

"It sure does auntie Becca."

"It feels great to me, now fuck me harder I'm getting close again." Doris said.

Timmy started banging harder and that pushed Doris over the edge.

"Oh my God! Fuck, fuck, fuck, I'm coming!" She announced and then punctuated that statement with several squirts and spasms around the boy's cock. Timmy held himself tightly inside her and pulsed out his own orgasm, filling her box with his steaming load. Doris collapsed on the bed and onto the now soaked towels and Timmy followed with his softening cock still inside. When he rolled off he said.

"Wow auntie Doris. That was great."

"Yes it was young man. Just remember when you need a roomier pussy to pound to come visit your auntie Doris"

******

A week later Tonya and Rebecca enjoyed a thoroughly hot mutual masturbation session watching the recording of Timmy giving it to Doris. The two friends were relaxing together on the sofa but knew the time was quickly coming for them to make themselves scarce if Rebecca's promise to give Timmy some alone time with Madison was to be honored.

"I can't believe how much she squirted." Tonya said.

"You should have seen it in person. I think she got some on me as close as I got to them recording this."

"Well I'd love to see her squirt like that and maybe make her do it."

"That's not going to happen unfortunately." Rebecca said. "She declined my offer to do just that but has taken several opportunities to resample our young stud's talents this past week. She's been like a kid on Christmas morning playing again and again with her favorite toy. I guess there was a lot of pent up juice in that gal."

"She doesn't get him tonight. I hope she understands that." Tonya said.

"Of course she does. She did ask about his availability though when she stopped by this morning before her shift. She was a bit disappointed but gets that he has his date with Madison today and is off limits to all of us. I told her that I was even forgoing my morning bang."

"How big of you my dear. I'm pretty sure that you've had more of his dick to this point than Doris and I have had combined."

"He does live with me you know."

"And he should be back here any time now with her so let's turn off this video you have of him fucking us one by one and put these toys away. That was quite a nice little film you cobbled together by the way. You could have a future in porn directing."

"Oh my, you're right about the time." Rebecca said, and then they both heard the sound of Timmy's key turning in the lock. Some panicked hustling from both women had the evidence of their afternoon playtime hidden before the two young people were fully inside the apartment. Rebecca quickly switched off the living room tv with the remote and Tonya gathered the toys and ran back to Rebecca's bedroom where she tossed them hurriedly into the nightstand drawer. Fortunately they were both completely dressed but hadn't been for that long. It was almost as if they were subconsciously hoping to be forced to confess their ongoing sexual dalliances to young Madison.

"Hi Rebecca." Timmy said to his somewhat flustered auntie. "I hope we're not too early. I think I said we'd be home around now."

"No, you're not early Timmy." Tonya said, emerging from the bedroom and looking a little flustered herself. "We lost track of time looking at some old recorded memories of fun times we had when we were younger."

'Yeah, a few weeks younger,' Rebecca thought but didn't say. What she did say was, "Did you kids have a good time this afternoon?"

"Yes we did." Madison answered. "I took Timmy on a tour of wine country. It was a beautiful day to be out and about."

"And now you're in and we're going out." Tonya said. "I suppose it's the way of things, in and out."

Madison thought she caught a wink exchanged between Tonya and Rebecca and she had frankly been surprised when Timmy had told her that their boss was spending the afternoon with Rebecca. Timmy reminded her that these two women had been his mother's closest friends and they still were very close to each other.

"We should be getting a move on Rebecca. They won't hold our reservation forever."

"Where are you guys going to eat?" Madison asked her boss.

This stumped Tonya because they in truth had no reservation anywhere but were going instead to hang at Tonya's place while the two youngsters had the time and space they needed to get intimate.

Rebecca came to the rescue with. "It's a little Italian place near the wharf that you probably haven't heard of. We may go to a club afterward so you kids have a good time. The old ladies won't be here to cramp your style."

"You're not so old Rebecca, neither of you are." Timmy said.

"Why thank you Timmy. You are such a gentleman." Then to Madison she said. "Do you remember what I said about being careful?"

Madison nodded yes in response and then Rebecca and Tonya waved goodbye on the way out the door.

"What did she mean by that be careful remark?" Timmy asked Madison when the two women had gone.