Show Moms Ch 04 05

DISCLOSURE: If you're looking for a sex-filled romp featuring a younger guy and an older woman, this probably isn't the story for you. Allow me to recommend "The Accidental Gigolo," my attempt to write exactly that kind of story. Just click on my name above, and you'll find it on my member page under Stories/Poems. Despite the sex that introduces the following chapters and the "Mature" category this story falls in, this story is actually much more of a romance.

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 to the state finals 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? Your husband must make you pretty happy then, huh?"

"Allen? 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 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, 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? Of what?"

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

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

"It'll show her what she's lost, 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. Nobody in that division has ever come close to winning."

"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, I walked to the bike I had ridden 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.

"You got me a present?"

"Actually no," I said. "Open it up."

She tore open the wrapping paper and stared at the contents, a gorgeous red gown. There was a note on top from Becca: 'From one MILF to another. You'll do great! Good luck at States! Becca Roberts, MILF America.'

"Kenny, it's gorgeous," she whispered, pulling it half-out. "I can't accept this."

"Becca can afford it," I told her. "Besides, you remember what I said about winning the early contests?"

She nodded.

"Well, this will cinch it. Everyone has to wear a gown at those contests. So there are a whole bunch of women stripping them off at the same time. The only problem is making sure that you get the judges' attention while the striptease is going on. I guarantee you that the judges will be looking at you in this."

"Thank you, Kenny," she said. "Just . . . thank you. Time to hit go home and hit the weights?"

"Not today. You were right yesterday. It's time to move on. Terry's home in two weeks, right?"

"August 15th," she agreed. "I think it's a Tuesday."

"And after that, I assume we're not going to have a lot of time together," I said.

"That's true."

"I've seen you move, and I don't think we're going to have to put a lot of time in on your strip act. You have excellent rhythm, and you're very sinuous."

"Thank you, Kenny," she said, pleased with the compliment.

She was smart. I'd had to look that one up, too.

"But you do need to learn how to climax. Those judges can spot a fake a mile away. Probably from downloading too much Internet porn. So that's what you'll be doing today."

"I'll be doing? What about you?"

"Today's just for you. I want you to look at that book, practice with the dildo, and look at this CD."

I pulled out the CD I'd burned the night before.

"You'll need to put it in your computer. It's the tape of me at the MILF Show last year, with Becca Roberts. I told Becca about your problem — no, no, I didn't tell her your name — and she suggested that you watch this. It sounds wacky to me, but what the hell, she's a woman, you're a woman, what do I know?

"I biked over today," I continued, "so I'll just see you tomorrow."

I kissed her on the cheek — I was starting to kind of like this cheek-kissing thing — and got out of the car. I took the scenic route home, enjoying the fact that I hadn't been on a bike for a while. An hour later, I stowed the bike in the garage and walked into the house to hear the phone ringing.

"Kenny," my mom shouted from upstairs. "Is that you? Can you get the phone?"

I picked it up and never even got the chance to say 'hello.'

"I want your big, fat cock over here," the voice hissed, "and I want it now."

I was a little taken aback. Suppose Mom had answered?

"Fine," I said. "This time I'm coming through the front door."

That'll show her.

The front door was wide open when I arrived. Maybe it wouldn't show her. I leaned my bike against the porch and went in. I closed the door behind me.

"Robin?" I called. "Oh, my God."

At the top of the stairs was a vision in red. She walked down seductively, knowing full well that I was watching the way her breasts made the silk shimmer, and the way that her hips pulled the fabric tighter first one way and then the other.

"What about the Seventh Commandment?" I spluttered.

"I don't want to fuck you, Kenny," she said in a husky voice I'd never heard before. "I just want to see it.

"Couch," she pointed. I walked over to it feeling a little bit like Dr. Frankenstein.

"Turn," she said just before I reached it. She was directly behind me, and her voice scared the shit out of me. How could someone be that quiet in high heels on a hardwood floor? As I turned around, she dropped to her knees, and with one skillful tug, she had my sweats and shorts down to my knees.

"Just like on the tape," she muttered, pushing me onto the couch with one hand while she reached for my dick with the other.

She leaned forward, and with her lips mere millimeters from my rock-hard cock, she looked up at me.

"Tell Becca that it worked," she said. Then she dove forward.

I think this was the point at which she really bought into the whole MILF Show thing. Because this was the point at which it became her MILF Show. I was apparently done with my role as coach. I was once again just a handler. I just leaned back and enjoyed it. Robin told me later that she'd given blowjobs back in high school, but that Allen had seemed to enjoy them less and less as time went by. Finally, their sex had settled into little more than missionary work.

Her skills hadn't deteriorated a bit. I thought that Becca was a pro at this, but Robin had her beat hands down. And Robin wasn't even using her hands! When I opened my eyes to look down, I noticed that Robin's hands were both down in front of her, cut off from my vision by the blond head engulfing my cock. In what seemed like seconds I was on the verge of exploding.

"Robin," I mumbled, "I'm gonna cum. Robin. Robin, I'm cumming."

I finally heard the muted "mm-hmm" from deep in her throat, and I stopped trying to hold it back.

She tried to swallow all of it, but it was just too much. Well, that coupled with the fact that her hands had supplied her with her own orgasm just seconds after I started spraying. Moaning, she collapsed forward onto my lap, letting the rest of my cum spill out of her mouth onto my groin. Finally, she pushed herself erect, with a quick look to make sure she hadn't spilled anything on the gown.

I figured it was time for a snappy remark.

"Well, there's one problem we don't have to — " I started.

She slapped me. Hard. Right across the face. I was stunned.

"Ouch," I whined.

"Don't mock me, Kenny," she said. Apparently it hadn't been that time.

Robin's face settled back to its old self as she wiped a strand of cum off of her cheek with a finger and pulled a towel out from underneath the couch. Advance planning was important.

"How long has it been for you?" she asked with some surprise as she began cleaning me up. "Or do you always cum this much?"

I thought back. It actually had been a while. Between my morning training sessions, my late afternoon caddying (I could usually fit in a second round, although it meant going until just about dark), my weekend caddying, shit — I hadn't fucked anyone in three weeks. What kind of high school graduate was I?

"Three weeks," she pondered after I told her. "Hmmm."

"What?" I asked finally.

"I think it would be a much more effective presentation if you can give me this kind of effort at the state contest, don't you?"

"Oh, sure," I laughed. "I'll just stay celibate during my first semester of college."

That was a great idea. Didn't everybody do that?

"I think that's a great idea," Robin agreed.

"Are you kidding?"

"No."

Obviously she wasn't.

"Look," I said, "you can't expect me not to have any sex for the first, like, seven weeks of college. It's just . . . it's unreasonable!"

"Kenny," she answered me. "We've been working on this for two months now. I know it started off as a lark for you, but it's become important to me. Even beyond the twenty thousand dollars. When I was sitting in front of my computer, watching you and Rebecca Roberts, I decided that I was going to start taking this just as seriously as she did."

"Right up until the Seventh Commandment," I said.

She smiled at me.

"As you've pointed out, Kenny, no woman my age has ever won a state tournament. I don't have any unrealistic expectations. And don't worry, I'll give you a blowjob after the local contest and the intercounty contest. We have three weeks between that and states, don't we? That way we'll make sure you don't ruin it with some adolescent wet dream."

I was speechless. And when I left, a few minutes later, I was apparently committed to being some sort of collegiate monk.

We continued running for the next two weeks, but for the rest of our mornings, after our breakfast, we worked on Robin's performances. By the end, she could strip off the red gown with practiced ease, and tease me with the black bra and garter-and-stocking set she was going to wear underneath. She'd turned the dildo into an extension of her fingers, and I found myself wishing that Moses had come down with only nine commandments. I was jealous of a nine-inch piece of plastic, for crying out loud.

And she sucked my cock. Man, could she suck my cock!

The final day we'd have to ourselves was a Monday, the fourteenth of August, and we decided to make it a dress rehearsal for the whole fall campaign. We'd do everything: the striptease, the masturbation, and the blowjob.

We'd finished our morning run and Robin had driven us back to the house. She was going to make me a real breakfast to celebrate — steak and eggs — and I'd just gotten comfortable on the couch downstairs when I heard the door open.

"Mom? I'm home!"

Chapter 5

Robin finished blowing me with a flourish, taking a long, loving lick up the entire length of my cock.

"What do you want now?" I asked her harshly.

The dialogue was our own addition. Last year, Becca and I had had to wait until she was one of the five women selected from her division to do the compulsory routine. With only ten women in Robin's division, though, all of the contestants had to do the compulsory, and had to do it immediately after the blowjob. There was nothing in the rules against a little dialogue for the sake of transition, and I knew from last year that the whole arena was miked to let the audience hear the sounds of sex. The script, of course, was all Robin's.

"Fuck me?" she said submissively.

"I beg your pardon?"

"Fuck me," she whined.

I reached down and grabbed her underneath her arms. By this point, she'd dropped enough weight to allow me to lift her fairly easily, particularly since I'd done some of my own weight training with her over the summer, and kept it up in the Handley gym that fall. Our compulsory routine this year was cowgirl, requiring her to ride me for five minutes. It had turned out to be a fairly poor choice so far, with the earlier contestants just riding up and down their handlers' poles. Robin, of course, had come up with a variation.