Cynthia’s Man Training

Daren, home for his first shore leave from Norfolk since he joined the Navy, banked a shot off the boards, putting the desired ball into the pocket, and high fived with his high school buddy, Steve. While Daren went off to the Navy, Steve had stayed in Lexington, Virginia, to work in his uncle's garage rather than opting for either college or the service. Charlie, the third of the trio who had gone through school and gotten into trouble with the other two and who was struggling through his first year in community college, stood by, wisecracking that he didn't think he'd ever seen Daren sink a pool ball before.

Daren countered with the nonsensical, but understandable, quip that if Charlie hadn't sunk one too many balls, he could be off enjoying a ride on the sea with Daren. But then he apologized when he saw the look on Charlie's face go gloomy, saying he'd maybe picked up the curse of opening his mouth too much from the company he'd kept in the four months he'd been in the Navy. It had been a double hit. It had been Charlie who wanted to go into the Navy, and Daren had picked up that bug from him, and most of why Charlie was struggling in community college was because he'd gotten Shelley pregnant the night of the senior prom. He was having to hold down a job at Steve's uncle's garage to support them and the coming baby as well as going to college as his parents wanted him to do.

The trio was at a roadhouse bar just outside of Lexington, to the west, and although they weren't old enough to drink hard liquor, the owner of the bar turned a look the other way for locals and this was the only place in or near town they could enjoy pool and whiskey. After a couple of shots of whiskey to establish they could do it, they switched to beer, which they refused to admit they still preferred.

Daren was bent over the table, ready to take another shot, when Steve nudged him and whispered, "Look what just drifted in. Gotta be 36 double D jugs. Wouldn't you like to get your dick into that hot momma while you're on liberty?"

"The momma part is right. She's old enough to be Daren's momma," Charlie said.

"Them's the best ones to give a young guy a good ride," Steve said. "But did you have an opportunity to get your first ride yet, Daren, baby? They got mermaids out there in the ocean giving out to young sailors?" He and Charlie both chuckled. Daren did not. Sometimes it wasn't a good thing that three guys had been glued together since elementary school. They knew too much about each other. Steve was in the same boat as Charlie. He actually gotten there before Charlie had. His baby with Brandy was due around Thanksgiving.

Despite being, by far, the best looking—and now best squared away—of the three, with his blond, sunny looks and milky-blue eyes, Daren couldn't claim expecting any bundle of joy before next spring. He hadn't been the best looking of the three when "doing what comes natural" came to the guys before graduation and they started drifting apart, two of them into the arms of girlfriends. Daren had been on the pudgy side then. It had been the conditioning of becoming a sailor that had brought him into body beautiful territory. And his dad had been busy dying in the spring when the other two had found sex, so he'd been too preoccupied to go that route . . . yet.

"Yeah, she's a real honey," Daren said, not responding to the "have you been laid yet?" burning question. "I'm surprised she don't fall over on her face when she walks. A good face and Earth Mother hips and big butt. A hot momma for sure. I missed my shot. You're up, Charlie." He'd been looking a Cynthia, who had come into the roadhouse and rested her tits on the bar top, though, and, in looking around the room, Cynthia had seen Daren looking at her. Daren didn't know it but Cynthia was man trolling for someone just like him—a hunky young guy to enjoy and give a little training to. The acoustics in the bar were better than the young guys thought they were; Cynthia had heard two of them razzing the real cute one on whether he'd been laid yet. She hadn't missed that he'd avoided answering that.

She ordered a beer and turned on her stool, leaning back to jut her best assets out, leaned her elbows on the bar top, and watched Daren play pool while he took furtive looks at her. She'd quickly made her choice.

At forty-two, voluptuous Cynthia could still fill out a halter top and minishorts, with stiletto heels, really well. She had a good head of wavy auburn hair. It had strands of gray in it that she'd stopped fighting, but to the casual viewer, it looked like expensive, saloon-done highlighting. She knew that it wasn't her hair that men were looking at, though. They rarely looked above tit level when they addressed her. She called them Pride and Glory, and she didn't hide them under a bushel.

Cynthia wasn't a hooker, nor did she come out to the bars every night. She lived in a fashionable university neighborhood of Lexington and had a bundle of money from her earlier marriage and a good job editing complex and arcane medical journal articles and books in her home office, in a sunroom on the back of her well-kept Dutch colonial house in a well-landscaped patio garden. She didn't have to come out looking for sex from a hot young man at all, if she didn't want to, as she took in a variety of well-servicing male lodgers to keep her exercised. But now and again she wanted to let lose for an evening and, invariably, then she was in the mood for a fresh young thing to train. She was an expert in picking the guys needing honing out and landing them. This evening, in addition to bringing Pride and Glory into action, she was getting help from the young sailor, Daren's, buddies, who egged him on in giving Cynthia his virginity.

In Daren's dad's truck, in the roadhouse parking lot, Daren was sitting in the driver's seat, with Cynthia sitting in his lap, astride his crotch, leaning back into the steering wheel. Her halter top was on the floor on the passenger side, and Daren's hands were cupping and squeezing her breasts. He had his face buried in her jutted-out chest and was panting hard as his lips sucked on her nipples. He hadn't been this intimate with a woman before, and Cynthia had had to do all of the maneuvering. She didn't mind this one bit, though. The kid was learning as they went along. She was latched into the cougar thrill of picking off a virgin.

She could feel him hard and needy against her puffy slit under the two layers of material that separated them from already fucking. Cynthia could have made minor adjustments and the young stud would be inside her, although he might not have known how they got there. Taking time out to bring in protection, though, might kill the mood, and she wasn't doing it without a condom. He was muscular and young and good-looking—a real catch of the day; Cynthia had every confidence he would manage to follow her lead and get it done. She was in it for a longer haul, though, and was only slightly annoyed when she felt the wetness "down there" from the young virgin being overwhelmed by the new and different action.

No biggy, she thought. She had planned to take this one home and training him at a more leisurely pace anyway.

She slid off his lap and onto the passenger side floor, coaxing him to move over into the passenger seat. Kneeling between Daren's spread knees, she unzipped him, told him to lay back and enjoy it, and fished his young guy, on-the-rise-again, shaft out of his fly and took it in her mouth. When he was moaning deep and fully engorged again, a gift of his youth and virility, Cynthia took the cock between her breasts and rubbed him off to a second ejaculation. Daren just sat there, mesmerized, arms dangling at his side, letting Cynthia do all the work, afraid that if he opened his eyes, he'd find himself back on his bunk on ship, dreaming it all.

He lay, trembling and groaning back in the seat after she'd brought him off a second time.

"You want to come with me for a while, baby?" she asked. "I live just inside Lexington. You can follow me in your truck."

There was no question that Daren wanted to go home with Cynthia for a while. He'd been aching for his first lay for months. Of course he was the one getting laid.

* * * *

Cynthia didn't take Daren directly upstairs to her bedroom when they got to her house in Lexington. She ushered him around to the red-block patio that covered nearly her whole small backyard.

"Have a seat and let's talk a bit," she said, as they entered the backyard and moved to where they would be sitting across from each other on wrought-iron patio chairs. She had a collection of wind chimes that harmonized in various tones in the breeze without becoming obtrusive. It would cover any conversation being overheard by any neighbors who might be lurking beyond the tall basket-weave wooden fences that gave Cynthia's yard privacy. "I'm going for a cold beer. Do you want one or do you want something harder?" she asked, as she motioned for Daren to sit while she remained standing. "You were drinking both at the roadhouse."

"Is that your way of asking me if I'm old enough to drink hard liquor? I'm not. I'm nineteen."

"It was," she said, "so beer it is. Is that OK with you? If you insist—" Virginia law was eighteen to drink beer and wine and twenty-one for hard liquor. The age of consent for sex was eighteen. An experienced cougar, Cynthia often asked the one question to get at the second answer.

"Beer's fine," he said as she moved toward the steps up into the sunroom attached to the back of her red-brick Dutch colonial. "But it's a little late to ask me if I'm too young to screw, isn't it? We've already messed around."

"Not like we're going to mess around now," she said, disappearing into the house and leaving Daren to think about that.

When she came back, she had a bottle of iced beer in each hand. As she gave Daren his she leaned over and, after a second or two, he managed to pull his attention away from her cleavage bound up in her halter top and participate in the kiss. She put her beer down on the patio table that was between their chairs but off to the side and kneed her way between his thighs for a closer embrace and another kiss. She drew his face into her chest, knowing that Pride and Glory were her best weapons, although in the light of the candles she'd lit around where they were sitting, she knew she looked damned good. Drawing away, she said, somewhat breezily, "Why don't you pull your T-shirt off? I'd like to see your muscles."

"Umm, I don't know—"

"If you take yours off, I'll take mine off," and she proceeded to pull her halter top over her head and deposited it beside the chair. His eyes bugging out, Daren shucked his T-shirt.

"There, very nice. Very comfy," Cynthia cooed. "And look at you, you stud. The Navy works you out to perfection. I need to make a trip to Norfolk to check out more fleet studs."

"Thanks," Daren said, nearly swallowing his words, gulping a bit because they were sitting so close across from each other that Cynthia, her legs crossed, could reach his shin with her dangling, stiletto-clad foot—and did.

"Now, that we've gotten comfy and established we could do this, I'd like to know, because it determines how we proceed, whether you've ever fucked a somewhat older woman, like me." She was pushing it. She was over twice his age.

"Uh, no ma'am, I haven't." Daren admitted.

"Well, this is your lucky day. A woman a bit older than you are can teach you a lot. Have you fucked any woman yet? Be honest about it; it doesn't mean we won't be doing it. Have you made love to a woman or had sex with her—put your Roger there in her cunt? The two aren't the same, but making love comes after mastering having sex, and sometimes can be a disappointment in comparison. So, have you?"

He paused long enough that Cynthia knew the answer, but she waited for it anyway, and he was honest.

"No ma'am. Some petting, but with older women? No, except what we just did in my truck."

Cynthia laughed. "What we just did in your truck is puppy play compared to what we'll do upstairs."

Daren visibly shuddered, but there was a silly grin on his face.

"So, did you come prepared, Sweetness?"

"Prepared?" he asked, dumbly but then caught on as she gave him an amused look. "Oh, you mean rubbers? No ma'am. Does that mean—?"

"That doesn't mean anything, love. But lesson number one in your training: Sailors always come equipped and use the equipment before they come. After tonight carry your own condoms around with you wherever you go. You'll never know when they'll be needed, and, frankly, you're such a handsome stud I can't believe you haven't had woman crawling all over you to get to it already."

"I've shaped up since joining the Navy," Daren said, "and I've pretty much been out to sea with mostly guys since then."

"Well, we mustn't let you experiment with guys and finding out you swing that way. It would be a loss to womankind." Cynthia gave another hearty laugh that made her tits shimmer and made Daren almost fall out of his chair in hardening lust.

"Well, when you finish your beer, we can go upstairs," Cynthia said in a cooing voice.

Daren nervously chugged his beer.

* * * *

"Gently, gently, baby. More centered." Cynthia was on her back at the foot of her bed. Daren was kneeling between her spread thighs. Both of them were naked. Daren's blond head was buried in Cynthia's crotch, and he was doing his best to follow her directions for pleasuring her. He was fumbling it, though, which she had expected, and hadn't quite seen the evidence yet that spending time turning her on would reap benefits for him. Both of his arms were extending up, his hands clutching and squeezing her breasts. Cynthia had left him to that, as the tit work seemed to be his fetish and he settled down better to follow his natural instincts when he had contact with those.

"Baby, baby, baby," she murmured, taking his head in her hands and moving it up, trying to show him where the clit was and that he'd have to dig for it with his tongue. He was coming awfully close to lapping at the wrong hole. First things first. That should be left for advanced training.

He lifted his head and muttered. "Shit, I don't think I can hold off much longer."

"It's OK, baby. You're young," she sighed. "We can pick up on this later."

It wasn't going to be a chariot ride through heaven this time, but she didn't expect it to be. It was just nice to think how young and handsome and well-built he was. And she'd been pleasantly surprised at the length of his erection when she was giving him head before going on her back and telling him she'd show him what he needed to know to get the most pleasure out of a woman.

"You want women coming back for it, don't you?" She'd asked.

"Yeah, of course."

"So, what do you think will make them do that?"

He'd looked at her with a dumb look on his face. "Having a big cock and screwing her good?"

"It's something before that, baby. If you want maximum pleasure you need to give her maximum pleasure too. And the secret to that comes before sliding your cock inside her."

He'd given that a dumb look too, but he was willing to learn, so she was showing patience with him. Indeed, training a new guy, especially one as good-looking and sweet dispositioned as Daren was, was a big turn on for Cynthia. He just was fresh and having a hard time controlling himself, and he was excited. She knew there would be a lot of releases short of her ultimate pleasure before this one graduated from the course. The training was worth it, though, she thought.

"OK, baby," she said. "Go for it. But just a minute . . ." Daren had popped up from between her legs and was waving his erection at her, anxious to get it in. "Protection first, baby," she said "Over there. The condom. Hand it to me and I'll do the honors. Never be so anxious that you don't think of protection, though."

Daren stood there, groaning and shaking as Cynthia split the condom packet with her teeth, extracted the disk, and rolled it on his shaft with both hands. "Steady. Hold it, baby. Learn to release on your command. Now, now, now. Oh, fuck, baby!"

He was in, leaning over her, his hands pressing down on her shoulder tips, not obsessed with her breasts now. Obsessed with being inside a woman for the first time. Doing what came natural now. Moaning, Cynthia raised her legs, hooking her ankles on his shoulders. She really liked it when the man fisted her ankles and held them raised, her legs spread wide, while he fucked her in a missionary. But that would come later in Daren's education. He hadn't caught on yet that it was about pleasure for both of them and finding out what it was and building on that. That could come later too. This was his first full fuck. He'd never forget it even if it lacked refinement. She wouldn't deny him his first pleasure.

And it was good even if it didn't last long. Good for him as a first effort. Good for her as another notch on her bedpost, with such small victories getting less and less frequent as she grew older and as she had increasing trouble maintaining the body that young men wanted.

And it didn't last long. Daren had fallen easily into the rhythms of procreation and just let his shaft do what it was designed to do. But he was young and fresh and this was all overwhelming to him. Five pumps and he came, filling out the bulb of the condom, and collapsing onto Cynthia's body. A few seconds of exhilaration as he savored the first-time accomplishment, but then doubts and a dive in emotions as he sensed he'd come too fast, that she'd show her disappointment in his performance.

Cynthia embraced his trembling body and held him to her. "That was great, baby," she whispered. "You're a stud. We'll make it even better." He was still inside her, going flaccid, but still long and inside her. She moved his face down to her breasts, and he settled in to suckling her nipples.

Her gaze went beyond him to the doorway of her bedroom out onto the second-floor landing. The door to the second bedroom, the one where she housed her men lodgers was across the landing. Standing in her doorway, though, leaning up against the door frame in just white briefs, holding a bottle of beer in his hand and grinning, was her current lodger, Billy D, twenty-three, tanned, with wavy dark hair, Italian, and built.

* * * *

"First time?" Billy D asked. It was Cynthia he was asking.

"Yes, he's doing fine," Cynthia answered, patting Daren on the back as he suckled at her breast. Hearing Billy D, though, caused him to rise and turn, looking shocked.

"At ease, soldier," Billy said to him.

"Sailor. He's a sailor," Cynthia answered.

"Lucky you; you get to ride the waves," Billy D said to her before addressing Daren again. "She's one fine piece of woman and you can get more pleasure out of her than that what you messed up there. You go on over and sit in that chair over there and we'll show you how this can work real good."

Snuffling, Daren pulled away from Cynthia and went to a chair near the bed and sat, as Billy D directed. Billy D laughed and handed his beer bottle to Daren in passing. Reaching the foot of the bed, he said, "Spread your legs, little darlin'. Let's show this young buck how to do this right."

Cynthia did so. "See these, and this, and this?" Billy D said, addressing Daren and fingering Cynthia's privates, moving to spreading folds to expose the clit. "See this here, this is the G-spot, the source of a whole lot of pleasure for women. You pay this good attention—not too rough but not too soft either, and you got a woman who will ride your cock like a rodeo rider. Watch this."

Billy D went down on his knees between Cynthia's spread thighs and pressed his face into her pussy. He went to work with his lips and tongue and teeth, while letting his hands roam around on her voluptuous body, paying particular attention to her breasts. Daren watched closely and in increasing awe, as Cynthia was turned on and began to moan and groan deeply, to grab Billy D's head between her hands to hold him in place between her thighs, and to writhe and thrash about as he went about his business of working her clit and folds and slit with his mouth and fingers. Only when she arched her back, cried out, jerked repeatedly, and collapsed back onto the bed with a long sigh did she stop writhing under him.