Cheryl and Meryl Pt. 03

That night, around eleven p.m., Cheryl and Jeremy heard a tentative knock on their bedroom door.

Cheryl leaped up from the bed—she was dressed in a baby-doll nightgown that only came up to the middle of her thighs—and opened the door. She found her father standing in the hallway. He was dressed only in his underwear.

Cheryl raised her eyebrows and smirked. "May I help you?"

"Jesus, Cheryl!" Daniel cried. "I didn't expect you to open the door!"

"Dad, this is my bedroom."

"I know that. But I just expected Jeremy to—"

"Well, he's not quite ready."

Daniel didn't know what she meant by that. Cheryl turned around to gaze at her boyfriend, who was lying on the bed, the bedsheet pulled all the way up to his chin.

"Okay, guy, it's time. Get a move-on."

It took Jeremy several moments to drag himself out of bed. He too was wearing only underwear, and he seemed as embarrassed as Daniel at his state of semi-nudity.

Cheryl looked at him with a frown. "What the hell are you wearing that for?"

"Jeez, Cheryl, what do you expect?"

"I expect"—and she marched over to him, flung herself to her knees, and peeled his boxer briefs violently off of him—"you to look like that!"

"God, are you crazy? I can't walk into your mother's room naked!"

"Jeremy, my sweet, you do know what's expected of you, don't you? Your performance tonight might be a bit hindered if you're still wearing this thing." She took up the underwear and tossed it contemptuously aside.

"I—I—" Jeremy blundered.

"Just go on in to Mom's room. She's waiting for you."

Jeremy shuffled out of the room, both hands on his groin. As he headed down the hallway to the master bedroom, he seemed to gain a bit of courage, and dropped his hands. But he still found that actually opening the door to the room—especially with a hand that was suddenly clammy with sweat—wasn't so easy. But at last he managed it.

He was sporting a fairly impressive hard-on when he walked into Shirley's bedroom.

She was sitting up in bed, wearing a long nightgown and turning the pages of a magazine without paying the slightest attention to the contents. When she saw the nude Jeremy saunter in, it was her turn to clap her hands over her eyes. A little squeal escaped her lips. This was, after all, the first cock other than her husband's that she had seen in about twenty years.

"I'm sorry, ma'am, it's just that—" Jeremy began.

"Never mind," Shirley said, now opening the fingers of one hand to peek at the sight in front of her. "Come over here."

Jeremy dutifully walked around to her side of the bed. He couldn't help noticing the long, heavy indentation on the other side, where Shirley's husband had been.

His erection was actually quivering uncontrollably. As he stood only a few feet away from his girlfriend's mother, she surveyed his abdomen with scrupulous care. Hmm, his thing is a bit bigger than Daniel's. I hope it won't hurt me. But she dismissed the thought. For God's sake, I'm not a silly young virgin! I'm a middle-aged woman who could be this man's mother.

That thought wasn't all that comforting either, so she tried to distract herself by seizing hold of Jeremy's cock with one hand, tugging it this way and that as if she was trying to uproot it.

"So," Shirley said slowly, "what exactly do you want to do?"

"Well, for starters," Jeremy said, "you could suck my cock."

Shirley pondered that proposition for a moment, then said, "Yes, I suppose I could."

She scooted down until she was lying on her side. At this angle, Jeremy's cock was right at the level of her head. As he edged a little closer to the bed, she opened her mouth and put as much of his cock into it as she could.

For a while she seemed to be in a sort of reflective mood, as if gauging how this organ differed from her husband's. Jeremy's was longer, but Daniel's was a bit thicker; and she now recalled that sometimes her mouth got sore from trying to open it wide and stuff his member in. So Jeremy's was a lot more comfortable. She didn't neglect his balls, for Daniel had drilled it into her head that nearly all men liked a woman to play with their balls. But she drew the line at putting those things in her mouth—much to Daniel's (and Jeremy's) disappointment.

After several minutes Jeremy drew his cock out and just gazed at Shirley. Wordlessly, he tugged at her nightgown and pulled it over her head, revealing the naked body underneath. He gasped as he saw it for the first time.

She was really quite beautiful. His eyes were instantly drawn to the full, heavy breasts, with their thick, protuberant nipples (and he couldn't help thinking of the twins suckling on them in their infancy—did they do it at the same time?), and her thick patch of dark fur at her delta. But the rest of her—from her delicately sloping shoulders, slight hump around her tummy, strong thighs, tapering calves, and round, firm bottom—was also enticing.

Shirley expected Jeremy just to plunge into her, but he had other ideas. Urging her to part her legs, he knelt down on the floor and buried his face in that hairy pussy, first rubbing his face against that tuft, then absorbing the heady, pungent aroma of her sex (subtly different from that of her daughters), and then pasting his lips against her nether lips, already damp and even dripping with arousal. He seized her bottom with both hands, glorying in their heft and curvature; and when he licked her clitoris for the first time, she let out a girlish squeal that amused him. She now pressed his head closely against her sex, yearning for release. She couldn't help recalling how, especially in recent years (before she instituted a complete ban on sexual congress), her husband would often be so heedless as to take care of his own needs without even bothering about hers, forcing her to stimulate herself after he had dozed off in exhaustion.

The culmination came far sooner than she expected. Her eyes widened in surprise as her orgasm, inspired by Jeremy's continual nuzzling, radiated out from her pussy all over her body, causing her to shake uncontrollably and emit curious gargling noises from her throat, her tongue lolling out shamelessly. He didn't let up in his stroking until she was compelled to thrust his head away from her sex, unable to endure any more pleasure.

"God in heaven!" she breathed. "That was incredible."

Jeremy, a somewhat smug smile on his face, stood up and gazed down on her. He gave her a few moments to recover, then got into position.

Strangely, Shirley felt like an inexperienced virgin as she saw this man loom over her. For God's sake, I haven't had a man other than Daniel in me for twenty years! A look of alarm, even fear, spread over her face—but Jeremy, sensing her distress, gave her a few soft kisses on the mouth and said, "Take it easy, ma'am—it's okay."

And he entered her.

As he proceeded inch by inch into that dripping twat, Shirley's eyes again bulged as she struggled to accommodate his cock's unusual length. She clutched him around the shoulders and wrapped her legs around his hips as he plugged her up to the hilt. Then he started pumping—gently at first, then more vigorously. He felt completely in charge as he squeezed and fondled her shoulders, back, thighs, breasts, and bottom with eager hands, and his penetration became so forceful that they elicited involuntary grunts from her in rhythm with each thrust. He knew he couldn't hold out terribly long either, and when the first dollops of his emission began, he buried his face in her neck. His emission seemed unprecedentedly copious, and even when he was finished he remained buried firmly in her. It was rare that he felt such a sense of unity—physical, emotional, and spiritual—with a woman. Somehow this was an altogether different order of experience than what he usually had with Cheryl (or Meryl).

At last he pulled out and flopped over onto his back next to Shirley. Her body was drenched with sweat—both his and hers—and she just gaped at the ceiling. It was clear that she had had an amazing experience as well. No words could possibly convey her feelings right now, and so she remained silent.

Like the wonderful young man he was, Jeremy reached over and encouraged Shirley to lie on top of him for some intimate post-coital cuddling. This was also something that Daniel had dispensed with in recent years, and Shirley almost shed tears as she snuggled up against his warm, taut body and relished his gentle massaging of her back and bottom. It didn't surprise her that, after some minutes of this, a certain bulge began to make itself evident in the area of his groin.

She looked into his face with a smirk and said, "Um, what's going on down there?"

"Sorry, ma'am, I can't help it."

"Is that my doing?" God, I hate fishing for compliments!

"It sure is, ma'am."

"You really want another go?"

"Yes, ma'am. But I wonder"—and here he pressed her bottom a bit more firmly than before—"I wonder if I could go in here."

No one had told him of Shirley's objections to anal sex, so he was taken aback when her face turned red and she said in a flat voice, "You're joking."

"Well, no, ma'am," he pleaded. "I kind of like it, and I hope you do too."

"Well, I don't."

"Okay, I'm sorry, we can—"

But she interrupted him. "I am never going to let a man do that to me," she hissed.

He was thunderstruck. The extraordinary intimacy they had enjoyed just a few minutes ago seemed shattered beyond repair. "But—but why?"

"Because it's vile and disgusting!"

"But how can you know that if you don't try it? You haven't tried it, have you?"

"No, and I won't—" Then a horrible thought struck her. "Don't tell me you do that to Cheryl!"

"Well, sure, she likes it a lot—"

"I don't believe that. You probably—" You probably force her . . .

"It's true, ma'am! You can ask her!" And, before he realized what he was saying, he blurted out, "You can ask Meryl too."

"Meryl!" Shirley shrieked, now in high dudgeon. "You did that to her?"

Jeremy blushed crimson. "Um, yes, ma'am. She—"

"And I suppose you did it the normal way too?"

"Yeah. She—she didn't want to be a virgin anymore."

"And you were happy to oblige, eh?"

"Yes, but—"

"And how did your girlfriend, Cheryl, react to that? Or doesn't she know?"

"Sure, she knows! She arranged it! She was there the whole time."

"She was there?" Now Shirley was livid with rage.

"Yes, of course! She was kind of supervising the whole thing."

"I see."

Shirley abruptly got up from the bed. Jeremy had to admit, as he watched the older woman standing there quivering with anger, that she had never looked so beautiful. He was convinced that she was about to order him from her bedroom, and in fact he got up himself and stood next to the bed. But then she said:

"How exactly do you want to do this?"

"What? Do what?"

"Go in my butt, you ninny! What else are we talking about?"

"But—but you just said—"

"I know what I said. But I'll be damned if my daughters—both of my daughters—can do something I can't do. If they can manage it, so can I!"

And with that, she jumped over Jeremy and landed on all fours on the bed, figuring that was the position he wanted her to be in.

"Um, ma'am," he said tentatively, "we need some lube. It'll hurt pretty bad if we don't use lube."

"Well, get some," she ordered.

He was reluctant to leave the room to fetch some cold cream from the bathroom. But he now saw a small jar of hand lotion on the nightstand. He squeezed some out on his hand and said, "This should work."

Before Shirley could protest, he applied the stuff to her anus. She wriggled and groaned in faint disgust, but didn't object otherwise.

When Jeremy told her to lie flat on her stomach, she said, "What? Why should I do that?"

"I think it's a better position for both of us."

She glared at him skeptically, but then said, "Okay, you're the boss."

As she extended herself in a prone position on the bed, he clambered on top of her and began the procedure. As he inserted the merest tip of his cock into her bottom, she whimpered pathetically—and tensed up. Jeremy pulled out and grabbed her bottom, squeezing it repeatedly and saying, "You gotta relax, ma'am. Just go limp—it'll be a lot better for you."

"I can't seem to do that!" she wailed.

"Just try, ma'am. Relax, take it easy."

His cooing finally had some effect, and she suddenly collapsed like a balloon with all the air let out of it. When Jeremy entered her again, her jaw dropped and her tongue stuck out of her mouth, but she managed to endure his invasion of her anus without too much fuss. As he got in about halfway, he figured that was good enough—and so he started pumping very gently.

"Is this okay, ma'am?" he whispered into her ear.

Shirley seemed on the verge of tears, but she managed to say, "It—it's fine."

He ground her hips into her a little more forcefully, also reaching around her chest to seize her breasts with her hands. She was truly and fully pinned under this tall, strong young man—and felt about as helpless as she ever had in her life. She didn't like that feeling, but couldn't figure out what to do about it. She just buried her face in the pillow and took his thrusts with weary resignation. Time stood still as he pounded her, minute after minute.

But all the enjoyment wasn't on Daniel's part. After a time he slid a hand down to her sex and began stroking it. The act caught her by surprise, and her eyes widened once again as she experienced a complex mingling of pain and pleasure such as she had never felt before. In some ways his pummeling of her anus was like repeated blows to her solar plexus; but his fondling of her pussy transported her to a new level of ecstasy. And when at last he sent his seed in repeated doses into her nether orifice, an orgasmic paroxysm of her own overwhelmed her almost to unconsciousness.

Jeremy pulled out of Shirley a bit hastily, causing her a twinge of pain in the process. He quickly dashed off to the bathroom to wash himself thoroughly. When he returned to the bedroom, he found his partner pretty much in the same position as before; she looked completely exhausted, but also highly seductive. He swept her up in his arms, placing her on top of him. She was still somewhat unresponsive, but he said in her hear:

"How was that?"

It took some time for Shirley to respond. She raised her head off of Jeremy's chest, gave him an inscrutable look, and said, "It hurt. A lot."

"I'm sorry," Jeremy said. "Really I am. But, um, didn't you come?"

"Yes, I came. Thank you very much."

Shirley assumed that, after two intense sessions, they would now drop off to sleep. But after a little more cuddling, Jeremy whispered, "Can we do something else?"

She couldn't even imagine what he had in mind. All she said was: "What?"

"How about sixty-nine?"

Shirley lapsed into silence, thinking to herself: You gotta be kidding me.

He misunderstood her quiescence. "You know what that is?"

She looked him in the face again. "Yes," she said, her voice heavy with sarcasm, "I know what that is." Heaving a huge sigh, she went on, "Oh, all right. Can I be on top?"

"Yes, of course! It's better that way."

Shirley made the effort to swing herself around so that her face was right up against Jeremy's cock—which, thankfully, smelled strongly of soap. She wasn't even concerned that her own orifices were dripping with his come (and some of her own juices); that was Jeremy's lookout. As she began the process of sucking and licking his long member, she almost got the feeling that this was some kind of obelisk that she was worshipping. Hah! she thought. Don't all men think all women worship this thing? She had to admit it was a most curious organ—really fairly small, all things considered, and yet throughout history (and even today) it seemed to play such a large part in man's domination of woman.

But she put those thoughts out of her head and did her best to stimulate the member, even though it was already rock-hard when she started. She didn't fail to pay attention to Jeremy's balls, which in some ways she found even more fascinating than the phallus. She reflected sardonically that, for all the power that the penis endowed to men, a little squeeze of those testicles could render a man as weak and helpless as a kitten. But she'd be magnanimous: all she'd do was give that sac a few gentle strokes and tickles with her long, slender fingers.

Meanwhile, Jeremy was delighted to lick up all the fluid dripping out of Shirley—and to induce more to emerge from her as he did so. The session was long and dreamy, and he sensed that Shirley came not once but twice while he nuzzled her and squeezed her bottom: almost identical choking sounds came out of her throat on two separate occasions, and she had to stop her own oral stimulation of his cock to enjoy to the full these unexpected orgasms.

The second one inspired Jeremy to send his third discharge down Shirley's throat, which elicited choking sounds of a slightly different sort. He could tell she wasn't all that comfortable with the procedure, but she bravely let the viscous substance slide thickly down her throat, even going so far as to lick up a final large drop of it that gathered on the tip of his cock. But immediately after he had finished, she flung herself off the bed and bolted for the bathroom.

Coming back, she slipped into bed. He could tell a slight but significant difference in her at once.

"You used mouthwash?" he said.

"Yes," she said. "No offense, Jeremy, but I really don't like the taste of come. And I don't want come on my breath all night."

"That's okay," he said generously.

"Can we go to sleep now?" she said. "I'm totally bushed."

"Sure. This was great, ma'am!" he enthused.

"Yes, it was, Jeremy. You're a treasure." And she gave his cheek a little stroke with her hand and kissed him on the mouth.

She seemed on the verge of getting up from the bed again, which led Jeremy to ask: "What are you doing?"

"I'm going to get a nightgown," she said.

He made a glum face. "I—I was kind of hoping you'd want to be naked next to me. Cheryl always stays naked after we, um, you know—"

Thanks for reminding me that I'm your girlfriend's mother. "I really don't like sleeping naked, Jeremy. I haven't done it in ages."

But his expression was so downcast that she relented. "Oh, okay. Anything to please my man."

She gave him one more little kiss, then turned her back to him. She generally slept on her left side, and she seemed to fall asleep almost immediately. Jeremy, still excited by this encounter with a creature in the full flush of ripe womanhood, tended to toss and turn a bit. After about an hour, he quietly raised up the bedsheet to get a look at his recumbent partner. The image of her flawless backside—especially that curvy bottom—was too much for him. He sidled over to her, also resting on his side. For a while he thought he might just slide his cock back and forth between the cheeks of her butt; that probably wouldn't wake her. But as he did so, he found himself unexpectedly slipping into her anus.

Since she was still a bit "open" and lubed from his previous entry, he went in without difficulty. In alarm he caught sight of Shirley's face. A frown appeared there, but her eyes remained tightly closed, and so he concluded she was still asleep. He tried to keep his thrusts gentle and unobtrusive. For a long time he didn't even care whether he actually came a fourth time or not; the sensation was so heavenly that it was quite enough for him. But as he sensed that he might in fact send another discharge into his beloved, he started pumping harder—and that caused Shirley's eyes to pop open.