Chapter 4

Trying not to cum was a difficult thing to do with my cock in Robin's mouth. For a thirty-eight-year-old mother of two teenagers who'd spent the last twenty years in Christian land, that woman knew how to give head. And as much as I'd like to take credit for it — and I like to think I played at least some role in Robin's having gotten this far — I had nothing to do with that part of it. Absolutely nothing.

Wally and I graduated on the Saturday after my talk with Robin. Wally was the valedictorian, just like his mom, and he took off on the following Tuesday as scheduled. His mother's training began the next day. With Mr. Kennedy at work from seven in the morning until five at night, Robin had the whole day free.

Robin didn't want anyone in her neighborhood to know what was going on, though, so at eight o'clock each morning, Monday through Friday, I'd run to a park about four miles from my house. Robin would drive over at eight-thirty, complete with her sweats, baseball cap, and sunglasses. I'd lead us in stretching, and we'd do some running. Afterwards, she'd drive us to her house — straight into the garage, of course — and get us some OJ and a bagel or English muffin. Meanwhile, I would I set up the free weights in the basement of her house. Apparently, Mr. Kennedy thought that the sole purpose of the basement was for the laundry, and had never set a foot there in his life. So we hauled in a carpet and an old couch and a bench and actually made it a pretty nice place. She'd bring down the breakfast, and then we'd hit the weights. Finally, when we were done working out, she'd drive me home, usually around eleven.

She made excellent progress. By the first of July, she'd gotten rid of the sweats and felt comfortable in running shorts and a T-shirt. After another month, she was wearing lycra shorts and a jog bra top. Her body looked great, and her hair was growing out nicely. In another week, we'd get it cut, so it could grow out a little bit before the first show on Labor Day weekend.

Plus, she'd turned out to be as pleasant as I'd remembered from when I was younger. We would chat over breakfast, and by the first of August we had actually become pretty good friends. She'd tell me what she'd heard from Wally and Terry (after a while I gave up reminding her that Terry couldn't stand me, and probably wouldn't want me to know what she was up to), and I'd tell her about my summer job, as an afternoon and weekend caddy at the club. She was even more pleased than I was when I told her about this one guy who had shot a hole-in-one, in part because he'd used the club I'd recommended rather than the one that he pulled out, which would have bounced the ball across the green into the pond.

"So there is some skill involved with this caddying?" she prompted me.

"Sometimes," I agreed.

"Just like handling a MILF," she teased me.

"Some guys require more caddying, some MILFs require more handling."

"Don't you think it's time for me to get some handling?" she said.

I looked up at her in shock.

"I mean," she blushed, "I'm supposed to play with myself, right? And give you a blowjob, right?"

"Well, yeah," I said. "But not until, like, the middle of October."

"And of course that's only if I win both the local and the intercounty," she said unsmilingly.

"Look at yourself," I said.

She looked at me, a question in her eyes.

"No, I mean look at yourself in the mirror," I said, nodding at the mirror we'd set up in one corner of the basement.

She walked over to stand in front of it, and looked back at me with shock.

"Wow," she said. "You've done a great job."

"Thanks," I grinned. "I had a lot to work with."

She grinned back.

"I wouldn't have thought this much," she said before turning back. She continued looking at herself, and then reached down and yanked the jog bra up and over her chest. Putting her hands on top of her head, she wiggled her torso, making her tits swing from side to side.

"God, I feel like a kid again," she turned her face toward me with a delighted look.

"You don't look like one," I choked out. I wish I'd had that picture when I was jerking off for all those years.

"So if getting states is a sure thing," she said, turning so I had an even better look at her, "I still need to learn to play with myself, right?"

"Learn?" I stammered.

"Well, re-learn, anyway," she said, pulling the top back down. "I haven't done it for twenty years, since I've been married."

"Seriously?" I asked. "Your husband must make you pretty happy then, huh?"

"Allen?" she asked. "Please. When he remembers to make love, he doesn't last any longer than he did when we were teenagers. No, it's me. It's like I can't... it's like I've lost the ability to climax. So I just kind of, um, stopped."

"Seriously?" I repeated. "Well, I know where I can get the dildo you need, and we need to go shopping anyway for the lingerie you've never owned. But climaxing... huh. Let me ask around."

"No names," she reminded me.

"Oh, give me some credit," I told her. "I might not have been the valedictorian, but I'm not an idiot."

"That's quite true," she gave me a kiss on the cheek. "You've done a wonderful job with this whole thing. I'm like your Galatea, aren't I?"

"Exactly," I agreed. I could look it up when I got home.

"And since you've gotten me this far," she said, "I think I'll trust you to do the shopping on your own. Now let's get back to the weights."

The solution to her problem, according to Becca, was quite simple.

"Show her the tape," she smiled later that morning. She'd been smiling ever since I told her, soon after I arrived, that I'd decided to enter the contest again this year.

"The tape?" I asked. "Of what?"

"Of us," she said. "You and me. The highlight tape. I had one girlfriend tell me she couldn't stop getting herself off every time she watched it. The fact is, you and I were really, really hot together."

"The tape," I said. "You think I should show this woman a tape of me having sex with another woman."

"It'll show her what she's lost," Becca said, "and help her get it back. All women can climax. Some just get these incompetent partners early in life, and they lose the feel for how to do it. I suspect that's what happened to your friend, huh?"

"Yeah," I nodded absent-mindedly. "Probably so."

"So?" she leaned forward. "Is she good enough?"

"To... ?" I prompted.

"Take down Connie Templeton," she slapped me on the arm.

"No," I said honestly. "Her goal is just to make it to the state final. Where she'll probably lose to Connie."

Becca frowned.

"If I have to give my MILF Illinois trophy to Connie Templeton," she said pointedly, "along with a check that I'm responsible for making bigger, I'm gonna be really, really pissed."

"Sorry," I held up my hands. "Maybe once she learns how to climax, huh?"

Becca laughed. The moment passed.

"Yeah, maybe."

Sweetheart that she is, Becca also volunteered to go shopping with me. I begged a day off from work, and Becca had no qualms about accompanying me into our little city's only sex shop. She even signed a few autographs for the, er, clientele. Then we got back into my car for a trip to the mall.

"Five six, thirty-six C, twenty-six, thirty-eight," Becca read off the list of sizes that Robin had given me. "Sounds nice."

"Yeah, she could probably get her waist down to twenty-five, but she looks better with a little more weight," I said.

"Which division?" she asked.

"Eighteen and up," I smiled.

"Oh, fuck you," she said heatedly. "You're not even trying."

"No, fuck you," I said with equal passion. "I'm helping out a thirty-eight year old mother of two college age kids who can't afford their tuition and who doesn't remember how to climax, and all you can think of is Connie fucking Templeton."

I concentrated on my driving, and the inside of the car was silent for an awfully long time. Finally, I felt a set of fingers tracing along my arm. I looked over.

"I'm sorry," Becca said. "You know, it's no wonder that I fell a little bit in love with you."

I furrowed my eyebrows in alarm and almost drove off the road.

"Just a little," she laughed. "Don't worry, Bob knows all about it. He knew back last fall. He's not going to beat you up or anything."

"Uh-huh," I said as we pulled into the mall.

It didn't take Becca long to approve some lingerie, and then she announced she needed to do a little shopping of her own. When we met again, twenty minutes later, she handed me a book and a wrapped package.

"'How to Please Yourself, '" I read off the title of the book. "Obviously for her. I'm already quite pleased. And this one's for me?"

"No," she laughed. "Something a little more personal for her."

"More personal than 'How to Please Yourself?'"

"It's a present for the lucky MILF you're handling," she said. "Tell her it's from your ex."

"Well, thank you," I laughed. "I hope."

She leaned forward and kissed me lightly on the lips. The trip home was a lot better than the trip there.

The next morning after our run, we got into Robin's car and I simply asked her to sit with me for a minute. I walked to the bike I'd used to get to the park that day, and fetched the bag I'd tied to the handlebars. We sat together in her car as I presented Robin with everything Becca and I had bought. She raised her eyebrows when she saw the lingerie, and looked a little alarmed by the dildo and the book. When I gave her the wrapped package, she just looked at me.