Chapter 9

When he got to her neck, he moved up onto her scalp, sliding his fingers through hair that smelled like perfume. He breathed it in and felt his cock twitch. It was still diamond hard.

He didn’t know what to do. He was finished with her back side, both literally and figuratively, but if he told her to turn over she’d see his ... condition.

She took the decision out of his hands by rolling over without being told to. Her eyes glittered, half open, watching him. He couldn’t be sure, but he imagined them going to the front of his shorts. If they did, she didn’t react, only lying there with her arms at her sides. Honestly, though, his eyes weren’t looking at hers. His eyes jittered in their sockets, moving all over her exposed skin.

He went back to her ankles. He’d worked her feet over already. Moving to her shins and then her thighs, he was treated when she moved her legs apart.

There it was ... her sexual core ... exposed and unprotected. Her pubic hair was lighter than the burnished copper hair that graced her head. There wasn’t an abundance of it and he wondered if she trimmed it short or it just grew that way. That she was relaxed was clear, though. Above her mons, where her abdomen was flat as a board, her hip bones stretched her skin outward. It didn’t make her look emaciated, though, possibly because her ribs didn’t show above that.

His eyes caressed her before he ever touched her physically, sweeping back and forth between her vulva and breasts, then moving to her face, now and then, to see if she was watching him ogle her. She wasn’t. Her eyes were closed. She looked very relaxed.

He worked her thighs and skipped to the sides of her hips, where those bones protruded. He moved the skin and tissues under it around where he expected her abdominal muscles to be, but merely stroked the part that covered only internal organs.

That brought him to her chest. He licked his lips.

“I’m going to touch your breasts,” he said softly. His voice felt dry.

“Okay,” she said.

That was it. All she had said was, “Okay.”

Trying to think of what he was doing as purely massage was fruitless. The widow and her sister were both in their early sixties. When it came to that relationship they were the ones robbing the cradle. Their bodies had been to more than one rodeo, but he didn’t care because he genuinely liked them. Their sexual activities weren’t the only part of his friendship with them. What they got from him was something they needed and loved, and he knew they felt good because of his attention. He’d been quite content with his monthly meetings with them. Stephanie had been a complete surprise. She’d astonished him when, after working for him for over a year, she had proposed he teach her the things she wanted to know about before she tried them with her boyfriend. She had no shame at all and her only caveat was that intercourse would not be involved.

Once they came to their “agreement” she had been an avid pupil, learning first to masturbate him and, based on what Bob did, how to instruct her boyfriend to masturbate her. Then had come lessons in oral sex, which she had loved even more. Initially she resisted letting him love her that way, but caved when he threatened to stop letting her “practice” on him. Recently they had both known it was more than “practice” but there was also consensus that this was just for fun, and not serious. Had they started a year earlier, it was likely she would not have saved her virginity for her boyfriend. That wasn’t an issue now, though, and she was old enough to exert the kind of self control that Bob both admired and honored.

The widow and her sister both had breasts that sagged, weren’t full or bulging, and were soft in ways that Bob couldn’t compare to anything else. Stephanie’s breasts were hard mounds with nipples that seemed embedded in the flesh, rather than perching on top of it.

Mandy’s breasts were of a different sort entirely. They were large enough to cup in both hands. They were firm, but heavy enough to pull away from her sternum in the position she was lying. Both her nipples and the areolas they sat on were dark brown. He’d expected them to be pink because she was a redhead. He knew that didn’t make any sense, but that’s what he’d anticipated. Her nipples were relaxed, but still prominent bumps.

He made no pretense, putting his palms on her nipples and rolling her breasts in circles, playing with them, exploring them, and even massaging them all at the same time. She made a small sound in her throat, but otherwise didn’t react to his ministrations.

Reluctantly he quit molesting her breasts and actually worked on the muscles that supported them. He then moved his fingertips to her cheeks and jaw, but admitted to himself it was just to touch her there, rather than as any part of the massage.

“I guess we’re finished,” he sighed.

“No we’re not,” she said, her eyes still closed.

“What’s still sore?” he asked.

“Nothing. I feel wonderful. You’re a good masseuse.”

“Masseur,” Bob corrected her. “But thank you.”

“Touch my breasts again,” she said.

He didn’t question her. He was also sure this was no longer a massage. His cock clenched in his shorts.

This time he gave in to playing with her nipples, squeezing them gently, pulling them this way and that, and rubbing his fingertips across them. They grew turgid and she made more noises.

He wasn’t sure she’d react well, but the urge to lean down and suck a nipple gently was too strong to resist. Her hands came to his head, but not to push him away.

Soon he was sucking like a starving baby, switching breasts as her vocal approval got louder. At one point it seemed like he’d done that enough, or that, if he continued, the poor nubbins would have to begin getting sore. He’d never spent that much time on a woman’s nipples before. The urge to kiss her was hard upon him, too, but he didn’t want to chance her rejecting that. He lifted his head.

“Do you need some ... internal massage?” he whispered. His hand went to lie on her belly, his fingertips barely on her pubic hair.

Her eyes were closed, her chest rising and falling rapidly. Her nipples still jutted out from her breasts, as if proud they could get that long. Her answer to his question was to spread her heels apart, bending her knees a little, and lifting her butt up off the bed.

Bob’s penis was leaking a bit as he slid his hand over her soft pubes, letting his middle finger find its way to the beginning of her split. In this, he had recent practice. Stephanie loved to cum on his finger and he loved playing with her and wrenching an orgasm out of her. With Mandy it was a little different, because she wasn’t likely to give him relief the way Stephanie would, sucking a load out of his balls. But once he’d given Mandy an orgasm she’d be relaxed and he could cover her up and go back to his room, where his hand would suffice nicely to empty his balls.

He paused long enough for the tip of his finger to find and circle her clit, flicking over it several times as her hips arched again and a groan seeped out of her throat. Without teasing her further he probed, finding that she was fully lubricated and sliding his finger deep inside her in one thrust.

“Ohhhh,” she moaned, as her tissues were spread. His digit felt different than anything else. She’d had other men’s fingers in her, but they weren’t like this, long and thick and rough. Despite that, he was gentle in a way that was completely unfamiliar to her.

Then he began moving his finger in a way that was astonishingly like what the rabbit did. It was fabulous.

She had no cares, no worries, no fears about what might or might not happen. She just lay there and enjoyed it. When his lips returned to her nipples it just added another dimension.

“If you keep doing that I’m going to cum,” she panted.

He stopped sucking long enough to say, “That’s the idea, silly,” and then went back to acting like a baby.

The orgasm, when it came, was unlike anything she’d experienced, at least as far as she could remember. It was as if she’d gotten overheated while running, desperately out of breath after a long sprint, and then staggered to a stop and flopped down on cool grass. Like a door swung noislessly open, allowing all her tension to flow out of it naturally, she felt intense relief and her body relaxed even more. It was clearly an orgasm, but it was sweet relief, rather than an overpowering, crashing thing. She felt like she was the sun, and her light was expanding to warm nearby planets.

He felt her internal muscles clamp down on him once, hold briefly, and then relax. It was her long heaving sigh of relief that told him, more than anything else, that she’d gotten “there.” It wasn’t what he expected, especially after hearing her cries the night before, but somehow he knew it was time to stop.

Gently he worked his finger out of her, knowing it might be “stuck” by her secretions. Once out, he slid his hand upwards again and, again couldn’t resist giving her clit a little circle, then patting it with his finger.

The urge to kiss her was upon him again and he hoped she wouldn’t react badly. He didn’t think about the absurdity of a kiss being more intimate than he’d just been with her. His lips brushed hers and her eyes opened.

“That tickles,” she said, reacting to his beard sliding across her chin.

“Sorry.”

“Don’t be. I’ve never kissed a man with a beard.”

“I’ve never kissed you,” he said, smiling.

Her hand came up and pressed on the back of his head. That kiss was firm, but not passionate, clearly a “Thank you” kiss between very close friends.

“I need to go,” he said, as he pulled his lips from hers.

“Blue balls?” She smiled.

“Something like that.”

“Too bad Stephanie isn’t here,” she teased.

“Indeed,” he said.

She sat up so suddenly and quickly, transitioning from a completely relaxed woman to an energetic one, that it took him by surprise.

“Lie down,” she said, scrambling to all fours.

“You don’t have to,” he said.

“As I recall, we were supposed to trade massages.”

He was hungry to feel her touch.

He lay down. In the process his heavy cock fell towards his abdomen and the bulge in his shorts was less pronounced.

“I can’t massage you that way,” she said.

“Oh, sorry.” He turned to lie face down.

She slapped him on the ass hard enough that it stung and he jerked.

“That’s not what I meant,” she said. “Get ‘em off.”

For some reason he couldn’t explain he stayed where he was, face down, working his shorts down over his hips and lifting them to get them past his jutting boner. At the last second he expected it and wasn’t surprised when she “spanked” him again.

He rolled, his shorts still around his thighs, and let her look at what she’d done to him.

Both understood that only one part of his body was going to be massaged.

Mandy had seen this thing before, but it had been from a distance, while she was feeling guilty, and it was being mostly hidden by Stephanie’s eager mouth. Now it was right in front of her and she could examine it closely. She tried to think of an adjective to properly describe it.

The first thing that popped into her mind was ‘intimidating,’ based on her reaction to Harold, the first time she’d held him in her hands. Her thoughts at that time were along the lines of, “No way. It will never fit. There’s just no way it could be anything but painful.”

That said, she had no trouble reaching for this new, live one. Her initial impressions of Harold had lasted only as long as it took to slide it deep inside her. Now her initial description of Bob’s phallus evolved as well. The adjective changed to “heavy” and was then supplemented with “hard” and “soft” and “alive” before she stopped thinking about adjectives and began to explore in earnest.

Matt’s penis had been circumcised and had a peculiar color change where the skin had been cut. From the head an inch downwards, the skin was almost white and then changed abruptly to his normal skin tone. His balls had been sprinkled with light hairs. He’d been four or five inches long.

She didn’t remember Tony’s appendage other than what it had felt like inside her, but Steve’s had been smooth and pink, also circumcised, though larger in diameter and maybe half an inch longer than Matt’s. She hadn’t spent a lot of time examining Steve’s. When he was home she was more interested in it being inside her, rather than being an object of exploration.

Ryan’s penis had been curved in a way that made it look almost deformed. The bare head of his manhood was purple and angry looking. When he was soft it was almost never longer than a couple of inches. Its shape had not caused any difficulties in having sex, except that he didn’t try to pull very far out of her for fear it would pop loose.

This one, only the fifth she’d ever seen in person, was a beast of a different kind entirely. She smiled as “beastly” was added to her list of adjectives, because it fit in so many ways. There was hair a-plenty surrounding the base and covering large balls that gave the impression of being swollen more than they usually were. The skin was dark and the surface bumpy, almost gnarled. She tried to imagine what Stephanie must have thought, the first time he bared this to her. Mandy would have been terrified at that age. She was sure of it. She wasn’t terrified at all now, though.

One difference from the others was its size in general. Bob sported a tool that was seven inches long at a minimum. Her fingernails, now cut and filed, failed to meet by an inch or so as she gripped it. The most amazing thing to her, though, was that even though she was gripping him firmly, her hand moved easily. On the others she’d had to let her hand slide over tight skin that didn’t move. Some kind of lubricant had been helpful with those. This one let her move her hand the entire length of his prod without loosening her grip in the slightest. She knew instinctively this was a product of the fact that his foreskin was still there. As her hand moved down, the skin moved off of the head, which reminded her of a small plum. Ryan’s penis had been pointed, like a blunt spear. His uncle’s was more towards a battering ram kind of shape.

“Am I doing this right?” she asked, moving her hand up and down slowly.

“Don’t fish for compliments,” he said, lifting his head to smile at her. “There is no wrong way to do that.”

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The City Girl Blues

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