Babysitter Cupcake: MILF Cuckqueaned

"Hello Barbara, this is Cassandra; Tiffany gave me your number," Cassandra greeted (after she'd come all over the senior girl's face and sent her on her way).

"Oh, hi," Barbara greeted. "I wasn't expecting a call so quickly."

"Tiffany said she thought it was urgent," Cassandra explained.

"Oh well, she may have been exaggerating a bit," Barbara replied, although it was true she'd wanted a response ASAP.

"Well, I'm free the next couple of evenings," Cassandra offered, even though she would readily shuffle her other appointments if need be for the opportunity to take control of a new couple... especially if they were as delicious as Tiffany claimed they were.

"I was hoping for tomorrow," Barbara said, deciding that even though she still wasn't comfortable leaving her children behind for an evening, she and Glenn desperately needed a night out together... and if Tiffany trusted this girl, she was almost certainly a safe choice.

"What time do you have in mind?" Cassandra asked professionally, inwardly excited by the possibilities lying ahead.

"Six," Barbara answered, "although I'd love you to come over a little early so you can spend a few minutes with the boys before we leave."

"Certainly," Cassandra agreed. "I'll be there at 5:30."

"Sounds great," Barbara agreed, finally getting somewhat excited by the possibility of a night without whining, crying or changing diapers.

Cassandra explained her rates, which Barbara found quite reasonable when she considered she was hiring a girl who was technically an adult as well as very experienced. "See you then," Cassandra finished.

"Good night," Barbara replied before hanging up.

.....

Cassandra showed up the next day exactly at 5:30 in a blue blouse that deemphasized her large breasts, a skirt that went all the way to her knees, and black thigh highs... a look that made her look professional and mature instead of like a college student... a look that typically achieved two effects on the women she was meeting: it relaxed them concerning the safety of their children, but it also made them feel slightly insecure as they compared their mid-life appearance and body to hers... this latter effect quite purposeful as she immediately began the cucking of a wife without her prey even having a clue.

Barbara was surprised by how pretty the babysitter was, and was also surprised by how mature she appeared, not to mention her professional attire. Today's high school students dressed like sluts or slobs, sometimes both, and that annoyed her. "Hi, I'm Barbara, please come in," she greeted warmly.

"I'm Cassandra," Cassandra greeted, as she walked in and gave the MILF she was planning on turning a big tit-crushing hug.

Barbara was shocked by the sudden hug, she wasn't a hugger (one of the reasons she taught high school instead of little kids). She also couldn't help but notice the teen had a large pair of breasts very like her own.

Cassandra knew that a seduction was based on subtlety (usually), and therefore backed out of Barbara's space and said, also knowing the power of compliments in building trust. "You look amazing for having two kids in three years."

"Thank you," Barbara smiled, appreciating the rare compliment she was receiving, as she added, "I still need to lose another twenty pounds."

"Don't we all," Cassandra said, fishing for a compliment, as she definitely didn't need to lose any weight at all.

Barbara scoffed, "As if you need to lose weight."

"I'm flattered," Cassandra said, taking Barbara's hand and giving it a squeeze... again, subtlety was the key. "So, can I meet the boys?"

"Of course," Barbara said, highly impressed with the pleasantness and beauty of this babysitter. She could see why Tiffany liked her so much. The girl was smart, sweet and pretty.

Barbara led Cassandra into the living room, where three-year-old Davis was playing with blocks while one-year-old Simon was lying on the rug.

"They're so cute," Cassandra crooned, as she reached down and picked up Simon and shifted to baby talk, "Aren't you just the sweetest thing, boo-boo."

Cassandra by the way, honestly did love children, especially babies, and had only discovered how this affinity could lead to sexual power when she'd been in high school and over a period of time had, to her initial surprise, ended up controlling her neighbour, which had awakened this predatory side of her. Well not predatory exactly, because her prey always ended up thrilled with their new lives.

"Not so cute when they keep you up all night or have another dirty diaper," Barbara said.

"Well, tonight you'll get a few hours without any diapers," Cassandra pointed out.

"That will be nice,' Barbara agreed. "Can you watch them while I finish getting ready?"

"Of course," Cassandra replied.

Barbara arrived upstairs just as Glenn got out of the shower. Glenn, who was wearing just a towel asked, "So how is the babysitter?"

"I hate to admit it, but I like her."

"Really?" Glenn asked, quite surprised.

"She seems very mature," Barbara added.

"That's great," Glenn said, relieved, as he walked over and kissed his wife on the cheek.

"Hey, don't get me all wet," Barbara objected.

"That's exactly what I want to do tonight," Glenn quipped, trying for flirtatious.

"Gross," Barbara sighed, no longer finding Glenn's sexual innuendos funny.

"You used to find my wit charming," Glenn pointed out, a little annoyed at his wife's prissy response.

"I did, but now it's just creepy," Barbara said, having no patience with Glenn's constant come-ons.

"Whatever," Glenn said, giving an overly dramatic sigh.

Barbara sighed herself before retreating to the bathroom. "Why don't you ever turn on the fan when you shower?" she yelled back to him, a constant reminder she had to give him, which by now annoyed the fuck out of her.

Glenn just sighed again, partly because she made a big deal out of every fucking picky thing, and partly because he'd forgotten again. He knew he only made matters worse by not remembering these simple things, but they just weren't things he found important, and thus he constantly forgot. He hated how she made such a massive deal out of such trivialities.

Barbara just wished he'd stop acting like he was an eighteen-year-old pervert; she was a mother of two now and not some college slut... although there had been a time when those same words had led to his cock sliding into her mouth for a delightful bonding interlude before they fucked as she loved feeling it slamming inside her. Fuck, maybe I am becoming too much of a prude.

As Barbara shaved her legs, something else she seldom did anymore (and was only doing it now because Glenn had promised her a special evening), she decided to make more of an effort. She even went so far as to trim her pussy, although she didn't shave it completely since she hated that feeling, especially when the stubble started growing back.

Barbara next did her makeup and hair. She put on pantyhose for his sake and a cute, sexy red dress that showcased all three of her best assets: her big tits, her tight ass and her fit legs.

Although Glenn had been stewing in annoyance, that state ended the moment his wife walked out, all dolled up for the first time in two years (that time had been for a wedding). He stared at her, reminded of just how beautiful she was; something men take for granted when they see their wives every day. "Sweetheart, you look amazing."

"You look pretty hot too," Barbara smiled, admiring him in a nice suit and tie. That was normal, he wore a suit and tie every day to work, but this time she was looking at him, really looking at him, instead of seeing him as just another feature in the generic chit-chat daze of each morning or each arrival home. She too had succumbed to the basic continuity of marriage and had been taking him too much for granted. She'd married him after all, and that had been because he had many qualities she really liked.

"Well, let's go and enjoy a nice festive night," Glenn said, as he glanced down at her nylon-clad feet (his fetish) but was disappointed to see her toenails weren't painted, and the nylons had reinforced toes. He preferred sandalfoot nylons that clearly showed her sexy toes, and he loved them painted (something she hadn't done in so long he couldn't recall the last time).

"Sorry, I ran out of time to paint my nails," Barbara apologized, knowing he liked them painted, and that she hadn't done them since before Simon was born... it was just too much effort to bend over and do it, and she wasn't about to pay a babysitter just so she could go get a pedicure and manicure.

"No worries," he reassured her, although he was more annoyed by the reinforced toe pantyhose... he couldn't fathom why she still owned a pair after all this time.

Barbara knew he was annoyed, although she wasn't sure if it was from the earlier conversation, the unpainted toenails, or the reinforced hosiery... she just thought they were more practical financially, and she hadn't bought any in over a year, since pantyhose were silly when she was at home with the kids, and reinforced ones were more practical for work, since they didn't tear so easily. Plus, since she dressed in the mornings after he left (he had a long commute into the city since they lived in a suburb) and since she undressed from work before he got home, he never had to look at the hosiery he called 'disgusting'. She actually liked how sheer nylons showcased her legs, the only body part that hadn't been affected by two pregnancies in three years, but she could care less about what style the toes were.

They arrived downstairs and Glenn could barely hold in a gasp as he caught sight of their babysitter... also in nylons... but these ones were indeed sandalfoot and her well-groomed toenails were painted sexy, seductress red.

Both Barbara and Cassandra noticed Glenn's staring at the babysitter's legs and feet. Cassandra had long ago learned the power of nylons... as many men were turned on by them, and even some women, especially older women, saw them as body enhancements to their physical package: something today's generation didn't understand, or if they did, they didn't care enough to put the effort in.

Cassandra walked over to Glenn with Simon in one arm, and greeted, "Hi, Mr. Barry, I'm Cassandra."

And then like she'd done to Barbara, she pulled him into a hug (one-armed), letting him feel her large breasts (which may not have made their normal impression on this man, since his wife also had a nice pair of tits... it was really impactful for men whose wives had small tits).

Glenn was surprised as he felt her breasts molding themselves against him.

Barbara was surprised and couldn't decide whether the girl was being friendly or brazen.

"Nice to meet you too," Glenn said, trying to act casual as his cock hardened from the dual delights of the babysitter's stocking-clad feet and her breasts briefly pressing against him.

"You two look dapper," Cassandra complimented, using a term from the past, and also one that was safe within the context of polite conversation.

"Thank you," Glenn said, as he glanced back down at the babysitter's sexy sheer showcased toes.

Barbara noticed where his attention rested and prompted, "We should get going."

"Sure, sure," Cassandra nodded, wiggling her toes temptingly, easily able to read this hot DILF (Dad I'd like to fuck), or the term she'd created herself, DIWF (Dad I will fuck). "Have fun."

Glenn was captivated by the sheer nylon toes, something he hadn't seen much of in the past couple of years except occasionally at work when his loan officer Pam wore open-toed heels, and of course, online where he often searched out pantyhose feet or watched scenes where women were being fucked in nylons without heels on.

"Thanks," Glenn acknowledged, in a daze.

Barbara took charge of his hand and led him to the door. They put on their shoes and headed out.

Once they were in the car and moving, Glenn offered, "She seems nice."

"You sure liked her," Barbara accused, her tone not happy.

"What?" Glenn asked, playing dumb.

"Don't pretend you didn't find her hot," Barbara challenged.

"She is quite pretty," Glenn agreed, trying to play it somewhat safe, knowing he was on dangerous ground here... truth be told, he felt he was standing on quicksand and could sink through at any moment.

"You were pretty much drooling," Barbara stated.

"Not a single drop," Glenn denied, confident that no drool had actually left his mouth.

"I wasn't being literal," Barbara said with a frustrated sigh.

"Look, let's not fight," Glenn urged. "Tonight is about us."

Barbara realized he was right. She was the one who'd hired a hot babysitter, and it wasn't Glenn's fault she was wearing the right kind of nylons, painted her toes and looked so hot. Barbara then realized that at least within her own head she'd just called the babysitter hot. "You're right, honey," she said, putting her hand on his leg and adding, trying to be sexy and playful, "It's not your fault I tempted you with a hot, slutty babysitter."

"Slutty?" Glenn questioned, surprised by her sudden shift from angry to sexy.

She rested her hand on his cock, not surprised it was hard, "Did our babysitter get your cock hard?"

Warning alarms clamored in his head. This was a trap!

Barbara continued, rubbing his hard on through his dress pants, not sure why she was suddenly feeling frisky, and enjoying teasing her clearly deer-in-the-headlights husband, "What got you going, dear? Was it her pretty green eyes, her flaming red hair, her big tits, her nylon-clad legs, or her painted toenails? All of the above, perhaps?"

"I plead the Fifth," Glenn finally managed, the best he could come up with as he groaned from his wife's hand on his cock. Very few women understand that one of the sexiest things she can do is to caress, squeeze or play with a man's cock while he's still dressed. It's a real turn on... as is, of course, dirty talk.

"We live in Canada, that isn't a thing here," Barbara refuted, as she continued rubbing his cock. "Go on, wax loquacious and try to dig yourself out, I dare you."

"Then I plea silence for marital peace," he said, pretty sure he was still in the danger zone... like when a woman asks if what she's wearing makes her look fat. If you tell her yes, you're being cruel and insensitive; but telling her no, that she looks wonderful, might appear to be the safer response, however if later on she decides you were lying and that you allowed her to appear in public wearing something less than flattering... well, then you're just an asshole.

"It's okay darling," she teased, deciding to be brazen, "If I were a lesbian, even I would fuck her."

"What's gotten into you?" Glenn asked with a groan as while he was still driving, she went so far as to unzip him and start fishing his cock out of his pants.

"Not this fine specimen for quite some time," she giggled as she struggled to get his cock out, having no idea what had gotten her so frisky.

"That lack can be rectified," Glenn said, as he rolled up to a red light and helped his beautiful wife get his cock out. She hadn't given him head in months, and she hadn't given him head while he was driving since the time they were traveling to the lake before the kids were born.

"Rectified? Okay, I'm giving you my rectum," Barbara joked, trying to be witty.

"I didn't mean that," Glenn apologized, as his cock was finally released from its confinement and fearing that one little thing could quickly end Barbara's amorous mood.

"I was kidding," she teased, as he resumed driving and lo and behold, she leaned down and took his cock in her mouth.

"Oh, God," he moaned, her lips wrapped around his cock feeling so good.

She only bobbed for about twenty seconds before he slowed down and she sat back up.

"That was awesome," he said, although he was disappointed it was so brief.

"We need to do more of this," she said, sitting back up.

"You blowing me while I drive?" he asked.

"No," she said, "just you and me. And doing whatever we decide to do."

"Agreed," he nodded, as he resumed driving, his hard cock still on display and saluting her.

Once they were inside the restaurant they chatted about work, they chatted about upcoming activities including Sunday's banquet for employees of his bank and their families, they chatted about whatever, the best part being they just got to be a couple, without the constant stress and interruptions of children. And they didn't bicker about anything. Not once.

As they were driving back home, Glenn asked, "So how is the babysitter getting home?"

"She drove," Barbara said.

"Good, because I'm wiped and I have to leave extra early tomorrow morning."

"So I'm not getting a hard fucking?" Barbara asked bluntly, although more for shock value. She too was kind of tired.

"I can probably fit that in."

"Oh, it would definitely fit in," she smiled, reaching over and giving his flaccid cock a playful squeeze.

"We definitely need to get a babysitter more often."

"Agreed," she nodded.

He yawned, "Hopefully the kids like her."

"Probably not as much as you do," she teased.

"You're the one who wanted to fuck her," he pointed out.

"Oh? And would you like to see that?" she teased with a sly smile.

"Would you invite me?" he asked for an answer, skirting his true answer: one million times yes.

"Would you prefer to see me between her legs or her between mine?" Barbara asked, oddly envisioning herself between Cassandra's legs. Barbara had had a few lesbian encounters in college and had really enjoyed eating pussy, something she hadn't done since graduation. The thought wafted into her head that Cassandra must have a sweet-tasting pussy.

"Now you're really testing me," Glenn said, even as he envisioned his wife between the teen girl's nylon-clad legs and remembered Barbara telling him she'd experimented some in college.

"I'm serious," Barbara continued, "if when we got home we found that sexy slut in our bedroom wearing nothing but her sexy nylons, what would you want to see?"

"You're serious?" Glenn asked. They'd occasionally talked about a threesome early in their relationship, mostly fantasizing about adding another girl, although Barbara had admitted once when she was drunk that she might fancy getting double penetrated or spit-roasted. Both were fantasies she hadn't fulfilled in her wild college years, but even with all their talk and speculation nothing had ever materialized, mostly because they both were worried about how they might judge each other the day after, and once their kids had appeared, any conversation about those topics had ended entirely.

"I am serious," she nodded. "Would you like to see her between my legs licking away, or me between her legs licking away?" Truth was, if she had her own way, she'd definitely be the one doing the licking, both because she preferred the submissive role and loved eating pussy, and also because she could tell by the way Cassandra presented herself that if she was lesbian or bi, which now in 2019 was a realistic possibility, that she would be more of a dominant.

"So a 69 isn't an option?" he asked.

"Perhaps, but answer the question," she continued.

"Am I involved?" he asked, knowing if he had his druthers, it would be the babysitter eating Barbara while he fucked the babysitter.

"You're involved, but only as a masturbating observer," she explained before adding, with the wickedest of smiles, "at least at first."

"You're driving me crazy," he told her, his cock once again rock hard.

She squeezed his cock and observed, "I have with me some firm evidence that you like the idea."

"Any man would," Glenn countered, which he imagined was true.