Madeleine Strays: A Wife-Watching Romance

One

It started on a Tuesday evening as the final month of the year arrived.

Hugo returned home after work to find Madeleine sitting at the little dining table between the TV area of the living room and the window seat. They didn’t really use that table other than for holding a fruit bowl—most of the time eating meals on the sofa in front of the television. But here was Madeleine, having drawn out one of the chairs usually tucked tidily under the table, sitting there peering at the screen of her little MacBook.

She didn’t even look up as her husband returned home from another hard day at the office, she was so absorbed.

“Hey honey.”

“Hey.”

She was wearing her glasses, which she also didn’t usually do either unless she was tired—or down. In fact, Hugo realized that they hadn’t really made much of an appearance in New York, certainly ever since she’d gotten her job at the bookstore. She looked cute in them—bookish, which seemed appropriate given her profession—and the look was emphasized by a high ponytail that seemed to be a light-hearted touch for Madeleine, but to Hugo gave her a coquettish hint.

“What are you up to?” he asked her quietly, dropping his briefcase by the front door.

“Oh, nothing much. I found this website.”

He took a few paces over toward the sofa, and now saw that Madeleine was wearing no pants. She sat in a white t-shirt, but after an initial moment where he thought she was naked, a couple of blinks confirmed that no, her shapely thighs were covered by pale pink leggings as she sat there, one hand subtly tucked between, the kind she’d wear to the gym.

What was she doing?

“What’s the site?”

“It’s called Mary-Kay. It’s a dating site.”

Hugo felt that oh-so-familiar flip-flop in his stomach, and a stirring between his legs. Dating site?

She must have picked up on his pause, seeing it as a hesitation. She said defensively, “We did talk about trying a stranger?”

Instantly he said, “Uh... Yeah... Of course.”

Trying to reassure her, spike any possibility she might think he disapproved. But Jesus, he thought to himself. This was really happening?

He approached her, placing his hands gently on her shoulders as he looked down at her screen, which was displaying a website designed tastefully in a lot of white with hints of pink and gray, which might have been an online florist or a wedding photographer’s site except that instead of floral bouquets or wedding packages for sale, the site seemed to be offering a whole load of different men for Madeleine’s perusal.

Hugo felt that familiar tingling pressure between his legs as his cock began to stiffen.

“A dating site, huh?” he said, trying to sound calm, interested but not panicking, despite the canon fire going off inside his chest. “So these are all what, potential dates?”

He gently massaged her shoulders and the back of her neck to underline his approval, his reassurance.

“It’s a dating site especially for extra-marital affairs,” she said, and he saw her shuffle her thighs together as though trying to cope with her own arousal. “I was actually wondering if you felt like helping me pick someone.”

Hugo’s eye casually tumbled through the headshots listed up on Madeleine’s screen. Shots of men that she might decide to ask out, to share an evening, a nice dinner and some drinks, a few numbers on the dance floor and a taxi home. Men she might go home with, strip for, take inside her until she was screaming out their name.

“Sure,” he said, leaning down to kiss the side of her neck, breathing in a hint of her perfume, yet also detecting the subtle scent of her arousal in the air.

As he kissed her, a glance down her top showed tempting cleavage bound in a sports bra, but somehow her nipples were just about visible through it.

She must have been seriously turned on.

Taking in the clues of her sports bra and leggings, he deduced: “You been to the gym this evening, honey?”

She smiled, looked up at him. “Yeah,” she said with that naughty lilt in her voice. “You think that got me thinking about dating?”

“Didn’t it? It’s been a while since we talked about maybe looking at this.”

She laughed, “Okay, maybe I was there. Maybe it made me hurry back here instead of taking my usual swim.”

He smiled, “And now you’re looking at lots of hot guys you might want to date?”

“Something like that. You want to take this into the bedroom?”

“Sure.”

She got up, and Hugo nearly choked as he saw the damp patch between her thighs. This girl was seriously turned on.

“Coming?” she asked him, walking straight past without apparently noticing that he’d seen just how wet she was already.

Hugo felt as though he’d crossed over into some bizarre other world as he quietly followed Madeleine through to the bedroom, her laptop clutched under her arm.

Were they really about to pick out a date for Madeleine, some lucky guy for her to seduce? It felt completely unreal. But here they were, Madeleine slumping down on her front on the mattress, opening her laptop to expose that dangerous website, which must have caused so much marital strife if it specialized in adulterous affairs.

Hugo lay beside her, his arm over her shoulders, one leg slipping over her nearest thigh, so that he was almost spooning her as they both looked at the Internet browser and the list of potential dates.

“So how far have you got?” he asked her, feeling things inside him churning and fluttering at the thought that his wife was using a dating site that sported the slogan “Enjoy life now—have an affair”.

“Well, I registered for the site, as you can see. Had to create a profile to do that…”

She clicked through to show him her page. The butterflies stirred in his chest as he viewed her details. She’d called herself ‘SexySiren31’, and included a headshot photograph Hugo didn’t recognize. When had she had that taken? Her eyes in the picture were blocked out by a black ellipse, but anyone viewing would be able to see how attractive she was.

Some straightforward details about her age, location, gender, smoking habits, height and weight came alongside her photo, along with a category called “Seeking” under which she’d put
short or long-term affair
. Jesus.

Then underneath that, there was a box which stated boldly: “Things I’m open to trying”. Hugo felt his manhood thicken up as he scanned through her suggestions. Setting aside the more nonthreatening answers like
kissing, cuddling,
and
sensual massage
, Madeleine had included certain things Hugo might have expected—
conventional sex, like to give oral sex, likes to receive oral sex, experimenting with sex toys
, even
blindfolding
and
bondage
, although those were something they hadn’t really experimented with.

There were a few things that had perhaps been prompted by their recent games—
likes to be watched
,
role playing
of course, but also
open to experimentation
.

But she’d also included a few things that made his eyes bulge.
Curious about domination
,
curious about submission
were there, as was
threesome
and
anal sex
, which was something they’d never done.

“
Threesome
, huh?” he said to her, pressing his hardness against her thigh.

She laughed, and wiggled her butt, which meant her body rubbing against his erect cock. “Don’t want them to think I’m boring,” she said.

“So what comes next?” he asked her, squeezing her gently in his arms, pressing his face to her cheek to kiss her.

“I search for my ideal man,” she said, clicking through to the search page.

“And he is…” Hugo smiled, kissed her.

“I don’t know… tall, dark and handsome?” she said. “Fit, tanned, impressive in bed?”

“Sounds like there’s one of those across the street,” Hugo said, and saw Madeleine gently blush.

“Well,” she said, “we’re not going there, are we? I think we’ll both feel safer with someone who doesn’t hang out at my bookstore on a regular basis.”

Hugo felt a slight pressure inside his chest merely from the fact that Madeleine saw Connor as a danger. It made him wonder whether the younger man from across the way might tempt her into a little more than just a one night stand if she gave him the chance. Sure, that did scare him, but it also excited him.

Madeleine put her requirements into the search boxes—tall, athletic, 25 to 50 years of age.

“Fifty?” Hugo said. “You want somebody that old?”

She smiled, said, “A little life experience—you know that could be sexy. A few gray hairs.”

Hitting the search button brought up a list of potential suitors. Madeleine flicked down through the list to the ones with pictures, but nothing seemed to catch her interest. There seemed to be a lot of guys on this service who were reluctant to include their faces in their photos, using either cut-off pictures, ridiculous looking masks, or photos that kept their faces in the dark or otherwise obscured.

“Do you really want to be with a guy who is already in a relationship?” Hugo asked her.

“No, you’re right,” she said, clicking back to her search screen to un-tick the option for
attached
males. “Hadn’t really thought of that.”

Again, the new search brought many profiles without a photo, and Madeleine skipped straight past them. On the next page of results, she scrolled down and actually found a youngish-looking guy from Queens, who had an easy-going kind of face, slightly wild overlong hair with a bit of a lazy quiff, and shades to slightly obscure his looks. He looked to Hugo a little like a Beat Poet, someone who might have hung out wit Kerouac or Ginsberg in the 50s.

“How come these guys still block out their faces?” Hugo asked. “They’re all single…”

“Fearful of vengeful husbands, I guess,” Madeleine laughed as she looked at her husband, who was the very antithesis of vengeful.

The guy’s preferences box seemed to list most—if not all—the same tastes as Madeleine, Hugo noticed.

His message was that he’d recently moved back to the area and was looking to meet up with new people, keep it simple with no strings. It made Hugo wonder why he was particularly interested in married or attached women—you didn’t use this website merely for dating single women.

Madeleine hit the button
add to favorites
, and Hugo felt a little ripple of fear and excitement jaunt through his body.

“Him, huh?” he asked her, giving her a squeeze.

“Maybe,” she said, blushing again. “But I’ll keep looking at the options.”

“You do that, honey.”

Hugo could no longer lie idly by her side. As she scrolled through all the tall dark and handsome strangers listed on her screen, he peeled off her top, and began to massage her shoulders and her back. She moaned as he coaxed her muscles, and was clearly enjoying his treatment of her while she cast her eyes on various men that some day she might want to sleep with.

When he reached for the bedside table to retrieve the small bottle of massage oil in there, he found she had already removed her sports bra.

It was a joy to touch her, to feel her smooth skin, and have her respond to his touch.

He massaged the muscles in her legs, and found himself sliding his face along her thighs, seeking out that wicked scent coming from her damp sex.

“How about this one?” she asked as he touched her. He pulled one of her knees up so that her legs could part, giving him easier access to her pussy.

“Looks good, honey,” he said. Her choices all seemed similar—showing a clear difference from her husband—yet a nobvious hint of Connor. Was she embracing the difference between these guys and himself? Did it matter?

He loved that she was doing this—actually looking for the right man with whom to explore The Fantasy. But his focus was increasingly less on the stream of guys she was looking at, and more at the beautiful goddess lying under him.

He dipped his nose between her thighs and inhaled her sexy scent, but unable to resist, he reached up to peel down her leggings, along with her drenched panties, and then while she shortlisted a handful of men she intended to send messages through the website, Hugo prized apart her legs, pushed up her hips and ducked down to taste her flaming hot pussy.

She raised her own hips a little more as he ate her, her moans telling him all he needed to know about how he was making her feel while she played with her dating website.

He couldn’t resist feasting on her while she was busy checking out an array of studs she might choose to fuck. It just seemed wrong on so many levels. He turned onto his back so he could slide under her for easier access, and she rested her pussy on his face while she continued with her website.

She was so wet, and the way she was unable to keep from gently writhing as he tasted her tangy slit was so appealing to him.

After a while, he heard her giggling, felt her whole body shivering from it. He rose to find out what she was up to.

“I have three guys trying to ask me out,” she said, giving him an impish grin that revealed how naughty she felt.

“You’ve been emailing them?” he asked.

“They have a messaging thing, like a Skype chat kind of thing.”

She closed her laptop, frustrating Hugo, who wanted to see what his wife was saying to other men, what the other men were saying to try to get her interested in a date. But he didn’t want her to feel she was being supervised. In this, he felt it important to let her reveal what she wanted to reveal.

She turned onto her back, and following her signals, he lay between her thighs and slid his swollen manhood inside her, in awe at how wet she was.

“You think you might want to go out with any of them?” he asked her breathlessly as they moved together.

“Maybe,” she said cryptically. “I told one of them you were licking my pussy while I was looking for a date.”

Hugo laughed. “I bet he thought you were a bad girl.”

She smiled. “He asked about you—I guess it just slipped out. Only seemed to encourage him.”