Madeleine Strays: A Wife-Watching Romance

by Max Sebastian

  That sounded about right. Hugo liked the sound of that. “What can I say? I started out hoping she’d get friendly with a few guys just to try to cheer her up after… well, after we moved to a strange new city. It came as a bit of a surprise that actually having her flirting with other guys would have such an affect on her.”

  “But you liked it, beyond the simple fact that it turned her into a horny sex goddess?” Connor said. He seemed genuinely interested.

  “I think maybe you wouldn’t understand it unless you have someone you can’t do without, someone so important to you that it would seem insane that you’d risk sharing her with other guys.”

  Connor nodded. “I’ve never really met a girl like that. A woman. Not until Madeleine came along—not that she’s the one I want to marry. But you’re not jealous? I find myself jealous sometimes when Madeleine’s with you now, and I’ve never ever been jealous about a girl before.”

  “I get jealous—and afraid. Afraid I’ll lose her, even though I know deep down that I won’t. But somehow, that’s become part of the thrill. You know—it adds intensity to the whole thing. A little like when you get that sharp fear on a roller coaster.”

  Connor signaled one of the servers to refill their drinks, and then he said: “You know, my whole life I’ve thought that when you got married, you had to settle for one woman and it would all get so dull. I kept dating all these different women, but they kind of all blur into nothing. I can see now the point of dedicating yourself to one person. But the idea that you would let her see other men, that it would strengthen your bond, that it would have the strange affect of making her more horny for you when she returned… well, I’ve never even thought about that before.”

  “It’s not for everyone.”

  “No, I’m sure it’s not, the amount of spousal homicide that’s caused by infidelity. But… well, recently, it’s begun to be something I can’t stop thinking about.”

  Hugo chuckled, a little disbelieving that the most eligible bachelor this side of New York, who they’d seen with countless young, beautiful women over in his apartment over the course of the past year, might want to find himself an insatiable wife to settle down with, while allowing her the same kind of sexual independence Hugo was encouraging in Madeleine.

  He said: “You could always give it a try. What have you got to lose? I’m not saying marry someone just to attempt that kind of experiment—but if you met someone who seemed right, you might give it a go.”

  Connor nodded. “You’re right. I should just do it.”

  *

  He actually enjoyed hearing from the guy his take on seducing Madeleine, on what it had been like for him to have no chance at this married beauty he saw regularly peeling off her clothes in the windows of the building across the street—and then suddenly find himself taking her out on dates, kissing her, going the whole way to heaven and back.

  “I think it was her attitude more than anything that was so sexy, so different to the girls I’d dated before,” Connor said. “She’s such a sharp, interesting person—and yet she has the most unbelievable fire inside her.”

  “She does,” Hugo said, feeling a warm glow inside him to talk about his beloved wife.

  “I don’t know how you guys can go your separate ways every morning to go to work. I’d want to keep her locked in the bedroom, never stop, you know what I mean?”

  “When you’re married, you get the feeling you have plenty of time for that. So you feel able to wait—long enough to earn a living, anyway.”

  “Well, I’d never cope, what can I say—your wife is so incredible.”

  Drinking with Connor, Hugo found himself actually wanting to hear the details of how the guy found his wife in bed, what they actually got up to. It was also fascinating to hear his side of experiencing the shared wife phenomenon.

  He said, “I think when I was first getting interested in her, the idea of pursuing a married woman just appealed because she’d want it no strings, you know? And then when she actually said yes—well, it was delicious to get something that should have been off-limits.”

  “I can understand that appeal.”

  “And then when we were on a date together—every time, it felt so different to any date I’d been on before. I mean, I date a lot of women, but it’s just so exciting being with Madeleine—she’s feeling this constant state of anxiety, that she’s being depraved or naughty for being on a date with you, and it’s just so hot.”

  Hugo nodded, understanding that feeling perfectly.

  “The first time we went back to my place for lunch, I remember how nervous she was. How she kept looking up at her place—at your place. Like she wanted you to be there, but didn’t.”

  Somehow, Hugo managed to remain stony faced. Somehow, he was able to raise his glass of beer without his hand shaking like crazy.

  “I think she was actually disappointed that you weren’t.”

  “Yeah?” Hugo’s throat was parched, despite the beer.

  “I mean, she quickly got over it. I remember it so distinctly. She was in these super tight jeans and a sweater that molded to her body.”

  Hugo knew the one. It was tight and scooped low enough to show off a healthy amount of cleavage. He hadn’t seen her wear it in more than a few months. His body buzzed at the implications. “The pink and white one? With the stripes?”

  Connor nodded. “That’s the one. We’d had a few lunch meetings. Been on a few dates. She’d been so coy, putting me off. I tried to be cool, but I couldn’t resist any more. Not with that sweater. So I suggested we pick up some lunch and eat it back at my place.”

  Hugo gulped. “And she said yes?”

  “Took some convincing, but yeah.”

  “And that was your first time?”

  Connor grinned. “First and second. We spent most of the afternoon together. She can be insatiable.”

  Hugo thought of the box of condoms and how empty it was. Everything started sliding into place. He felt sick to his stomach, but incredibly aroused at the same time.

  “She can be,” Hugo ventured.

  “I started thinking about her all the time—when we weren’t fucking, I mean.”

  “You did it a lot?”

  Connor looked up at Hugo, realizing perhaps for the first time that this was all new territory for the man. “Not as much as I would have liked. We had all our lunch dates at my place after that. We met up at the W a couple times, too, just to switch it up—she seemed to like that place.”

  Hugo could feel the panic in him rise as quickly as his excitement. She’d been fucking him all this time. Months and months of Connor’s cock in her sweet, adulterous pussy.

  “Yeah. We’ve had a few adventures there in the past,” Hugo said. He felt like a block of wood. His mind was on all those dates she’d had—dates in which she’d pretended to be seeing strange men. Dates she’d said led nowhere.

  Dates that he’d encouraged her to go on.

  “How did they usually go? Those times at the W?”

  “They were always my favorite. I love the casual Madeleine, but when she dresses up…” Connor shook his head. “I love a girl in thigh highs or stockings and short little dresses. Lainie never disappointed. And she seemed to love to get down on her knees in nothing but those stockings and heels and… Well, you know.”

  Hugo licked his lips and tried to swallow. “Yeah.”

  “Anyway, as awesome as those times were, it was nothing compared to the first time we did it with you watching. She was so nervous, and yet… I mean, she’d always been passionate, but that night, she took things to another level.

  “Yeah. You guys were pretty awesome to watch,” Hugo said. His shock had begun to clear. They were back in familiar territory.

  No, it wasn’t just that. Madeleine had actually done what she’d planned on doing all along: she’d had her secret affair, then slowly revealed it to Hugo. He’d encouraged her to sleep with other men—even knew that she might do it without his knowledge. How
could he be upset with her?

  Connor went on. “She’s really into you, man. She adores you. And I’m pretty fucking envious of that. I want to find a girl like that—one who’ll be so into me, but without being the kind of boring submissive sap that’s little more than a hole to fill.”

  “And maybe one that will embrace the idea of you sharing her? Hugo smiled.

  “Something like that. Hey, there was something else I wanted to talk to you about tonight,” Connor said.

  “Something else?”

  “Yeah. It was about Madeleine’s other relationship.”

  “Her other relationship?” Hugo’s body went cold.

  “Yeah. She won’t tell me about it at all.”

  Hugo scratched his head. “No, no, what d’you mean, other relationship?”

  “She didn’t tell you? I got a hint that something else was up, but then she wouldn’t say anything about it. I sure got the feeling she’s been dating someone else when she’s not with you or me—but she won’t open up.”

  “Seriously?” Hugo said, staggered. “But she was so nervous when it came to dating you. Like it was the first time.”

  Lucy hadn’t mentioned anything about this. Surely Madeleine would have told her if she’d been dating someone else as well. Then again, Lucy never told him that Connor and Madeleine had been fucking all long.

  Hugo felt queasy. Numb with shock. It was the same sensation he’d felt just a few moments earlier, when he’d realized that she’d been with Connor long before he’d watched—only a thousand times as strong.

  “I should ask Lucy about it.”

  “The chick she’s out with tonight? Her friend from college?”

  “Our Maid of Honor,” Hugo nodded. “Those two don’t have any secrets from each other. She’ll either know what’s going on—or else it’s not going on.”

  Hugo started typing a text message to Lucy. Connor interrupted. “You know any other men she’s shown interest in since you guys decided she could start dating again?”

  “A few. There’s a few guys she likes at the bookstore, one that she kissed once.”

  “She kissed someone? Maybe it’s him.”

  Hugo pressed send on the message:

  > Is Madeleine with you tonight? She said she was hanging out with you this evening, but I get the feeling she might be dating again.

  Connor said, “Do you think you might tell Madeleine you’re going to be out really late tonight? I don’t know, taking a client out, or something.”

  “Why?”

  He shrugged. “It’s probably a long shot, but maybe if she thinks you’re safely out of the way, she might think she can safely take a date back to your apartment for a few hours of play time.”

  “I see.”

  “We’d be able to see from my apartment.”

  Twenty Five

  They took a cab back, and Hugo felt the peculiarity of going into the wrong building—accompanying Connor into his apartment, somewhere he’d always thought would be the last place he’d ever visit.

  On the way there, he received a text message from Lucy.

  > She hasn’t told me what she’s doing tonight—what are you thinking might be happening? How late are you gonna be with your work friends?

  Hugo showed Connor the text, which suggested that if Madeleine wasn’t with Lucy, wasn’t with either of them—and there wasn’t an event or a late opening on at the bookstore that evening—then she had to be seeing someone new, or at least someone they did not count on her seeing.

  “Text her back to say that you’ll be out until very late with a client,” Connor said, then when Hugo looked confused, he said: “You know she’s going to feed whatever information you give her straight back to Lainie, right?”

  “I suppose.”

  Connor hunched his shoulders and turned up his collar as they exited the yellow cab, and Hugo realized the need for stealth—if Madeleine wasn’t back in the apartment with her date already, she might be on the way back, and recognizing her husband was now in league with her other lover might make her suspicious.

  In the elevator on the way up, Hugo saw that his new friend appeared to be nervous.

  “You okay?”

  Connor nodded. “I guess it’s a little unexpected, isn’t it?”

  “You don’t like the idea that Madeleine might be dating someone else as well?” Hugo asked, finding that actually, he was pretty relaxed about this whole deal himself. He’d wanted Madeleine to have fun with her sexuality, and this was exactly what she was doing if she was out dating another man.

  Connor, though, might be sleeping with another man’s wife, but he’d come to find Madeleine more than just another fling, and to find that other men might be sharing her was probably a new concept for him.

  “I’m not sure,” he said. “I mean, I’m the other man, so what right do I have to say who she should or shouldn’t see?”

  “I guess you’re right,” said Hugo, and suddenly did not envy Connor at all. Although he was the new exciting toy in Madeleine’s life, as a mere date he didn’t have the same kind of role as a husband if he wasn’t so keen on Madeleine’s other dating habits.

  “But it’s interesting, isn’t it? That she’s so free to see whoever she wants?”

  “I’ll say.”

  “Nice that she gets that excitement,” Connor said, as the elevator slowed to their floor. “If she’s pursuing her fantasy of an illicit affair again, she must be turned on like you wouldn’t believe.”

  “It’s a hot thought, isn’t it? You think of the look on her face as she’s misbehaving, as she’s being so wicked in bedding someone else.”

  It felt off to be teaching Connor the benefits of having an insatiable wife, almost like Hugo was trying to convert him. Well, when you discovered a wonderful thing, it was only natural to want to spread the word.

  “The thing is,” Connor said, “I now see the real benefit the husband has in this kind of arrangement. When Prom’s over, he gets to leave with the Prom Queen.”

  Connor’s apartment building was noticeably plusher than Hugo and Madeleine’s across the street—the fittings were nicer, the carpets in the hallways, but the most obvious sign that this was for wealthier types than them was the sheer size of the hallways, and as Connor held his fingertip up to the scanner on the wall next to his front door, letting them into a huge great apartment, it was clear in the square footage and the ceiling height of the apartments.

  Hugo felt an odd sense of familiarity with this apartment, having seen it so many times from across the street, most recently through a pair of opera glasses. But Connor kept the lights out after they came inside, and had them freeze just inside the door, in case anyone across the street was watching the apartment.

  Still like statues, they looked out of the floor-to-ceiling windows to see that the lights were off in the windows that Hugo assumed to be those of his own apartment.

  “What if they’re in there with the lights off?” Hugo whispered.

  Connor smiled. “You don’t have to whisper,” he said. “They might be able to see us, they definitely can’t hear us.”

  “Oh, right.”

  Connor was peering at the building across the street. He said: “They don’t have the blinds drawn, which Lainie would usually do if she was up to anything.”

  Hugo envied Connor his rich upbringing, to have an apartment like this. It stretched forever, with the kind of designer furniture, fixtures and fittings that made it look like some kind of movie set.

  “Nice place,” he said, for something to say while they waited like idiot statues.

  “Thanks.”

  “Always made my insecurity that much more intense, imagining Madeleine coming over here, wanting this instead of what we have,” Hugo said.

  “I think she’s perfectly happy with what she has,” Connor said. “A husband who worships her.”

  “It’s nice you can take her out on glamorous dates, though. She likes that.”

  “Ha
ppy to. Especially if I get to take her for a spin afterwards, so to speak.”

  “So to speak.”

  A few moments later, Connor was confident no one was in Hugo and Madeleine’s apartment, and they were safe to decamp onto a long sofa that faced away from the windows, and allowed someone sitting on it to peer over the back while concealing themselves—in this darkness at least—in the cushions.

  “So how come you call her Lainie?” Hugo asked, since he had Connor cornered.

  “Isn’t that what she’s called?”

  “Never. Or at least, not before we came to New York. She was usually just Madeleine, occasionally Maddie.”

  “She introduced herself to me as Lainie,” Connor said, getting up from the sofa seemingly with an idea.

  “I guess it’s her way of creating a new persona for herself—for her dealings with other men.”

  “A new persona—interesting.” Connor was in the corner of the large open-plan living area that appeared to be a study or office, complete with desk and bookshelves, ferreting through the desk drawers.

  When he came back, he carried two pairs of black binoculars, one of which he handed over to Hugo.

  “What was she like, before?” Connor asked him now, as they both peered through the high-powered lenses at the windows into Hugo and Madeleine’s apartment. “Before you came to New York, before you started feeding her this idea about dating other men.”

  Hugo sighed, as ever feeling it wasn’t his place to discuss Madeleine’s condition with anyone, particularly not her new lover. Playing it safe, he described Madeleine as the woman he’d married, the woman he’d fallen in love with.

  “Sharp as a straight razor, pretty as a peach,” he smiled. “But we were both fairly conventional back in Boston, you know. Monogamous, relatively conservative in how we saw dating.”

  “She never gave you any suggestions that she might like to see other men?”

  “Never. And I wouldn’t have considered it back then,” Hugo said. “If she so much as looked at another guy, I’d start getting all jealous and uptight.”