Madeleine Strays: A Wife-Watching Romance

by Max Sebastian

  She stood, obedient, hands placed on the back of the sofa, her beautiful behind presented for him. Hugo slid his full hardness between her cheeks, feeling the softness of her skin against his sensitive shaft, then he brushed the tip of his cock against her searing, slippery pussy lips.

  “I know how you like to dance,” he said as he teased her.

  She moaned, said: “He liked to dance, too. I could feel it.”

  “You could feel him? He’s big?”

  She nodded, biting her lip.

  Hugo thrust forward, entered her. She was dripping wet, he glided straight in, filling her completely, forcing out a blissful cry as his swollen organ touched every part of her inside.

  “He put his hands all over you?”

  She nodded. “I let him.”

  Hugo stroked her back as he fucked her tight pussy, loving the softness of her skin, the shape of her body, the heat of her flesh as she shivered and shook and gasped, this young doe he was reclaiming from another stag.

  He leaned down, over her shoulder, his thrusting slowing as she twisted her head to kiss him, giving him a glimpse of her wild eyes.

  She turned, and he gave her space to face him again, perch up on the back of the sofa, spreading her legs for him to step forward and glide back inside her glistening flower.

  “He touched you here?” he asked her, breathless as he fucked her hard, his fingers brushing over her lips before he kissed her again briefly.

  A slight nod, a wicked smile.

  “And here?” his hands slid down to her breasts, cupping her, fondling her, squeezing her, his thumbs grazing over her stiff, sensitive nipples.

  She nodded again. “Not on the dance floor. On the way home,” she said.

  “In those doorways.”

  “Yes.”

  “And here?” he slipped a hand between her legs, his fingers finding her moisture even as he continued to thrust inside her, then pressing against her clit to spur her on to greater levels of ecstasy,

  “No,” she said. “He didn’t touch me there.”

  “Maybe next time?”

  “Maybe next time.”

  And with that, she shuddered, she almost convulsed as her orgasm hit, her pussy squeezing him, pushing him over the edge with her.

  She was thinking about how another man might feel inside her, and seeing that in her eyes as he neared the end ignited a depth charge inside his chest.

  Hugo let the wave of emotion and sensation consume him, feeling the raw jealousy give in to the feeling that he was taking this beautiful woman back, making her his own again.

  But at the end, just after her climax blossomed, Hugo was pulling out of her, leaning back. A sudden hint of surprise passed through her face, but she allowed him to withdraw, stroking his head against her soaking, burning pussy for a few moments.

  Then his whole body jarred, and with his hardness gripped tightly in both hands, he pumped his hot seed over her pussy, his sticky cream spurting up over her mound, her stomach, splashing over her flushed rosy lips, her beautiful shaven pussy.

  Marking his territory.

  Nine

  Madeleine seemed to be walking on air the whole of the next week, and as a result, so was Hugo.

  They slept most of Sunday, feeling almost jet-lagged, they were so off schedule because of a night of rampant sex spurred on from her first date with Will. That evening, she revealed that he’d texted her, confirming a date for the coming Wednesday night, which they’d agreed on since Madeleine had the Thursday off that week.

  Only five days after their first date, it felt too soon to Hugo to be having a second date, though he could tell Madeleine was itching to see her new boyfriend again.

  That night they were too tired to even really talk about her first date. On Monday night, Hugo came home to find Madeleine sitting on the window seat, peering into her cell phone, one hand quietly tucked under her skirt.

  “Are you texting him?” he said to her, feeling the tickle of jealousy and the warmth of arousal stirring inside him.

  “Maybe,” she said, pulling her hand away.

  He smiled. “Don’t stop on my account.”

  The blinds were open, and Hugo could see across the street, though the more interesting windows were dark—even the college students’ place.

  “Oh, he’s finished,” she said, dropping the cell phone by her side on the window seat.

  As ever, she looked dazzlingly beautiful, sitting in the window with her knees drawn up under her chin, her hair tied up in a ponytail that allowed rogue strands of gold to hang down the side of her pretty face.

  A light went on across the street, and Hugo saw that it was in Connor’s apartment. Madeleine’s eyes seemed to light up—well, her crush was still firmly in place, then, even though she’d started dating another man. But then, no doubt she still reacted physically to Fabian or Ryan or Dan or any of her flirty authors, that wasn’t going to stop just because she’d found a new lover.

  “Does he still come into the store sometimes?” Hugo said, not needing to specify who he was talking about. “Does he still hit on you sometimes?”

  “Yeah, he does,” she said with a faintly dreamy tone of voice.

  “You still want him, don’t you?”

  “Of course,” she said. Her hand drifted back between her thighs as they watched him walk into his bedroom.

  “Well, maybe one day the opportunity will present itself.”

  She stood up, smiled, reached to kiss him. Her lips were so soft as they touched his—appreciating him, and his tolerance of her urges for other men, though perhaps her urges were in part due to his encouragement.

  “Did you have a good day, sweetie?” she asked him.

  “Sure.”

  “Want to make it a great day?”

  “Absolutely.”

  She reached under her skirt, and a moment later her panties were falling over her thighs and down past her knees to the floor. Then she slowly turned to the windows, leaning forward, her hands on the glass, pushing up her rear for him.

  “Fuck me,” she said, but he was already there, lining up behind her, sliding inside her incredibly wet pussy as they watched her crush on the opposite site of the street now strip off his shirt and his pants, turning away from them to the room’s built-in wardrobe before his underwear came down.

  Afterward, they were lying in bed together, and she said, “Lucy said you were suffering a little, while I was out on my date.”

  Hugo sighed, fearing that Lucy was now talking Madeleine out of this whole thing, their Maid of Honor not entirely understanding where he was coming from in all this.

  He said, “Waiting’s never easy. I wouldn’t exactly say I was suffering, though.”

  The thing was, part of him was in full agreement with Lucy. Only, along with the suffering, waiting in the company of the thought that his pretty wife was having the time of her life was also excruciatingly pleasurable.

  “Tell me what it was like, thinking of me being out on a date with another man.”

  He gently stroked her breast, noting how her nipple pursed, hardened under his touch.

  He said, “I guess it’s kind of scary. But also seriously hot.”

  “Scary?”

  “I was nervous, nervous that things wouldn’t work out, that you wouldn’t have a good time on your date. And maybe nervous that you wouldn’t come back at all.”

  “Oh, you know I wouldn’t do that to you.”

  He chuckled. “I know that, but the body isn’t always rational, you know? It depends on hormones that were never designed for this kind of fantasy.”

  Her fingers found his cock, saw that it was stiffening up a little.

  “I’m not sure I like the thought that I make you nervous when I’m out,” she said. She curled her hand around his shaft, appreciating its shape, its burgeoning thickness. Hugo noticed her breathing was deepening.

  “It’s not just nerves—all that just makes it seem more exciting, somehow. It’s hard to
explain. Like adding salt to your food—you wouldn’t want it all on its own, but when it’s there with the thrill of knowing you’re out enjoying yourself, feeling the buzz of a new relationship—then that slight sense of fear just enhances the flavor of everything else.”

  “When you’re waiting… you’re frightened that I might actually do something with my date?”

  “A little,” he admitted, then moaned quietly as she started to pump his shaft. “Only a little frightened—hopeful, mostly. I want to experience what it’s like to know you’ve been naughty, you’ve given in to your desires, you’ve stepped over the line.”

  “You’re hopeful I’ll be naughty?”

  “Yes,” he said. “To start with, even thinking you’re holding his hand, looking at him with that glint in your eye that says you’d quite like him to seduce you. Later, when you’d been out with him long enough, I start to hope you’ve kissed him, maybe found a dark corner somewhere for a little more…”

  She grinned. “So you would actually want me to… you know… go a little further, if the opportunity presented itself?”

  “I mean, I know I’ll always love you, no matter what happens. And the fact that I’m encouraging you to do this means I could never be angry if you actually go through with it. If I decide I can’t handle it afterwards—then I can’t handle it. But I know there’s no malice on your part, you’d never want to hurt me. So I want you to do it, find out what it’s like, so then I’ll know whether I want this to continue.”

  “End the uncertainty,” she nodded. Then she said, “What do you do when you’re waiting for me?”

  “Not a huge amount,” he said. “I do tend to dwell on my thoughts while I wait.”

  “You need some distraction,” she said.

  He shrugged, said, “You could give me some hints about what you’re up to.”

  “I guess I did kind of go all radio-silent on you most of the night, huh?” she said. “It was just too much to remember to text you, too overwhelming. Plus, I kind of thought I wasn’t doing anything worth reporting back, you know? Just chatting, drinking. A little kissing...”

  “It’s okay, I knew how it was. And I don’t want to feel like I’m controlling you.”

  “Well, maybe this next date I will do something worth reporting back on.”

  She kissed him, and it suddenly seemed so real, that she was actually going to be stretching these lips around Will on Wednesday night, smearing her lipstick all over his hard cock. When she slung a leg over his body, pulled herself up onto him, and he slid back inside her, Hugo wondered how he’d feel if he received a text from her saying that she’d finally fucked another man.

  Ten

  Wednesday. In the morning, he had to get up and out of the apartment before Madeleine. His kiss goodbye woke her, and still half asleep, there wasn’t much he could say that was in any way meaningful ahead of the evening’s date.

  “I love you,” he whispered.

  “Love you too, sweetie,” she said, lips curling into a smile.

  “Good luck this evening—enjoy yourself, let it go as far as you feel comfortable.”

  “I will.”

  “If you can’t manage to keep me updated—never mind, you can tell me after.”

  Then he was gone, his every spare thought that day revolved around Madeleine—about what kind of clothes she’d wear on her date to the symphony, about what kind of underwear she’d put on, about whether she’d be shaving her pussy again in the anticipation that this time they would go back to his place for a little fooling around.

  He thought about how nervous she must be in the run-up to the date, but how completely keyed up she would be, all day.

  *

  Nobody at the office was going for a quick drink after work, so come seven o’clock Hugo found himself descending the elevator alone, trying to decide what he might do with himself that evening.

  If this whole dating thing for Madeleine was going to continue long-term—and Hugo sincerely hoped that it was—he figured that he’d have to get himself some kind of hobby to pass the dead hours waiting for her.

  This evening, though, Hugo went through the security barrier of his building and out the door onto the street to find a familiar face out there waiting for him. Standing out there on the sidewalk in front of a hotdog cart was none other than the slender, Asian-American form of Lucy, arms folded, waiting for him. Smiling as he emerged from the revolving door.

  “Have we met somewhere before?”

  “Your face is kinda familiar.”

  She embraced him, a little more friendly than he remembered her ever being before, as though she had somehow accepted him as being more than just the husband of her best friend, as though they had a connection of their own now.

  Well, she did have a fairly intimate knowledge of his personal life.

  “You here to tell me Madeleine’s finally decided to run off with another man?” he joked.

  She smiled warmly, her eyes telling him everything was okay, that she was here to give him some distraction, to support him in this strange endeavor.

  “Maddie sent me down here to keep you company,” she said, and Hugo liked that this was the reason for her being here, that his wife was concerned about his wellbeing.

  “So she’s definitely planning on doing something tonight, then?”

  “Maybe,” Lucy said. She looked good in casual jeans and a Harvard hooded top, which Hugo knew she’d stolen from some boyfriend from ages past. “Maybe not.”

  Hugo chuckled. “So it’s going to be like that, is it? Should we go grab a bite to eat?”

  “Sure, that would be great,” Lucy grinned.

  “What you in the mood for?”

  “Comfort food, don’t you think?”

  They hopped in a cab for a short ride to a little diner over in Hell’s Kitchen that Hugo had been to a few times after work with Ray and Lowego. It had two rows of tables, and thankfully wasn’t particularly full for a midweek evening, so they got a booth by the windows.

  “Nervous?” she asked him once the order was in, and the waitress hustling away to fetch drinks.

  “Of course.”

  “More nervous than last time?”

  “Not sure. I guess a little more. I’m fairly sure she’s going to do something with the guy this time,” Hugo said.

  She nodded, leaned back. He couldn’t quite read her poker face: did she know something of Madeleine’s plans? It seemed to Hugo there was a faint glimmer within her pretty almond-shaped eyes suggesting she did have inside knowledge.

  Reaching forward to fumble with the straw in her Cosmopolitan, Lucy looked out the window, then straight at him. “How would you feel if Madeleine had an actual affair?” she asked him.

  Hugo felt a bolt of lightening scorch his heart. Was this the dark secret to which she’d referred the other night in her conversation with Madeleine? He managed to conceal his shock, play it down.

  He said: “I don’t know. I suppose it would hurt quite a bit.”

  “And yet here you are, and she is on a date with another man.”

  “This is totally different from an affair.”

  “How so? You’ve basically given her permission to fuck this guy.”

  “That’s the point, isn’t it?” he sipped his tall glass of draft Blue Moon. “I’ve given her permission.”

  “So it’s an affair, of sorts. You told her you wanted to watch her have an affair.”

  “I guess I did,” he said, nodding, never failing to be surprised at just how much detail his wife passed on from their private conversations to her best friend. “But I think you mean the kind of affair where I know nothing about it, and maybe it affects our marriage.”

  “If she did have something with someone, and didn’t want to tell you about it, how would you feel?”

  Hugo felt cold from this conversation, though the diner itself was wonderfully warm and cozy. He said, “I guess I’d feel excluded, and that would hurt. This whole thing isn’t ab
out giving her an alternative to our relationship—it’s about enhancing our relationship.”

  Lucy nodded. “You’d be angry at her?”

  “I don’t know.” He took a deep gulp of his beer, tried to imagine how he might feel if Madeleine came home one evening to reveal she’d been sleeping with Fabian for the past three months.

  He couldn’t quite picture it. Why would she do such a thing, when they’d been role-playing this kind of thing so extensively, and he had made it so clear she could date whomever she wanted—sleep with whomever she wanted—so long as she didn’t hide it from him, she shared the details of her entanglement.

  “I think if it was done because she simply couldn’t help herself, she was overcome by blind lust—I wouldn’t be angry with her. Particularly since I’ve been encouraging that kind of lust in her,” he said finally.

  Lucy tilted her head, taken aback by his response. “You’d be okay with it?”

  He shrugged, and realized as he was sitting there that actually yes, for the most part he’d be okay. “I’d be okay with the sex part,” he said. “Just the lying part, the failure to tell me—that would make me feel a little annoyed. Angry, maybe.”

  “You’d be okay with the sex part, but not the lying part,” Lucy nodded. “You saying the sex part would fit with this whole fantasy of yours?”

  Another sip of Blue Moon. “I guess part of me would find it exciting, yes. That she’s having a secret fling, that she’s being so hot and so bad. But that wouldn’t negate the fact she’d excluded me from this whole thing.”

  They watched as the couple in the booth across the aisle from them received two big plates full of burgers and fries. Hugo didn’t feel quite so hungry any more.

  Lucy said, “You both have this fantasy now, don’t you? For her to sleep with other men.”

  “I think so. I mean, I don’t like to think it’s just me pushing her to do this.”

  “Can’t be,” Lucy grinned. “Any woman looks at other guys and imagines fucking them, even if she’s dating Brad Pitt. But this fantasy—you know hers is probably a little different from yours?”

  “Different? How so?”