All You Have to Do is Ask

"You know, I've always considered myself a good girl, but here I was―a married woman having an affair with her boss. I think most women fantasize about things like this, but not many would have the guts to do it."

Dan looked amused. "Most women's husbands wouldn't encourage their wives to do it."

Matilda smiled from ear to ear. As small as it was, this was Dan's first admission that he hadn't merely passively accepted her behavior. He'd encouraged it. Even if he'd had a change of heart, surely she wasn't entirely to blame for what she'd done. Was she?

"I know I am extremely lucky," she said, her tone somber. "I will be paying you back for the rest of our lives."

Dan drew a sly smile. "You can start by telling me about the rest of the evening."

"We practically ran through the hotel lobby, and we started making out again in the elevator. He even lifted my dress to grope my ass. He slapped me, and I turned around and put my hands against the wall, inviting him to continue. He spanked me bare-assed, in the elevator!"

Her excitement made her speak fast, leaving no room for breaths between words. She had to collect herself before continuing.

"When the elevator reached his floor, he led me to his room with his hand on my ass."

"His room?" Dan questioned with a taunting grin on his face. "I'm surprised you even bothered to get separate rooms."

It was an odd joke, Matilda thought, but everything about the situation was odd. It had actually crossed her mind to book just one room. It would have been an unmistakable signal to her boss what she hoped would happen on the trip. She opened her mouth to say something along the lines of 'maybe next time,' but she caught herself. This had been a once-in-a-lifetime opportunity. That was the deal, and she shouldn't make Dan think she expected anything else.

"When we reached his room, we started making out again," she continued. "Even though we were extremely turned on, George paced himself. He slowly pulled my dress up as we kissed, and this time he didn't stop with just my ass exposed. He pulled the dress over my head then removed my bra. We continued making out, and it seemed he couldn't get enough of my body. There is something sexy about that contrast of being naked while he is still dressed; it makes me feel even more like I'm his slut."

The words leaping out of her mouth sounded shocking to herself, and she cautiously studied her husband's reaction. At first glance, his fiery eyes and flaring nostrils might have been misinterpreted as rage, but she knew him better. He was beaming with intense lust. She paused for a moment to let him savor the mental image she'd painted.

"But this time we weren't going to stop with just me undressed," Matilda continued. "He started removing his clothes, and I helped. I felt more than a little bit submissive as I kneeled before him. I removed his shoes and socks before unbuckling his belt. I hooked my fingers into both his pants and underwear, but I caught myself and didn't pull them down until I got an approving nod. I don't know how long I just sat there, staring at his cock. It's..."

Matilda stopped herself, thinking that what she planned to say was too much, but she had promised to be open and honest. She took a bracing breath before releasing her words.

"His dick is sexy," she said. "I guess it's largely because of who it's attached to―that it's exciting to know I make my boss hard. But it's also objectively good-looking―thick and beautiful. He gave me a slight nod, and I leaped right in. This was just the second time ever I sucked his cock, but it somehow felt like a familiar task, like we both knew our roles."

"Roles?" Dan questioned.

"Uhm, yeah. Like, he's the boss, I'm the office slut, and I should suck his cock whenever he wants me to."

Her words made her husband grunt. She yearned to release his erection from its restrictive confines and demonstrate exactly how she'd worshipped George's cock. But she paced herself. Dan had made it clear that he wasn't going to give her what she craved.

"Go on," Dan urged.

Matilda nodded, feeling both excited and nervous to tell her husband about the next line she'd crossed. "He likes how I use my mouth, and it wasn't long before he grunted like he was close to finishing. I was his to use as he pleased, so I didn't stop until he pushed me away. He had a wild look on his face as he looked down at me. He commanded that I'd get on the bed. I obeyed, of course."

She haltered, taking a moment to weigh her words.

"How did you lie?" Dan asked. "On your back or belly or...?

Matilda drew a smirk. Her husband sure demanded a lot of specifics. That didn't signal regrets. Then again, maybe he just needed to know exactly what she'd done to know what to accept or―worst case―not accept. She felt the knot tighten in her stomach, but a glance at her husband's tenting erection gave her hope. There was at least one part of him that still honored their agreement.

"I was on my back," she said, and excitement flushed over her as she remembered lying there naked, waiting for her equally naked boss to mount her. "He gave me a questioning look, like giving me one last chance to back out. I responded by spreading my legs. That anticipation as he moved onto the bed and on top of me... I can't even describe it. It's been ages since I had a first time with someone―not since you―and it's just, you know... I felt his cock rub against my leg as he crawled on top of me. And then it pushed against my..."

It was challenging to speak coherently when all she wanted was for Dan to take her, to reclaim his whore of a wife. She wanted to beg him, but something on his mind apparently needed to be resolved before they could reconnect the way she craved. For now, she had to settle for the excitement of remembering the night before.

"He teased me―or maybe both of us―by sliding his cock up and down my pussy. I wanted to plead with him to just fuck me, but I waited patiently. And then..."

She trailed off.

"Yes?" Dan urged.

"And then he did it," Matilda said.

Her husband grunted softly. Matilda leaned her head against his shoulder, partly because her mind was spinning with such lust that it was hard to even sit upright, but also because she didn't know how else to show her deep affection.

"Oh, honey..." she continued. "It was amazing. I know I've done things with him before, but to feel him inside me... It was so intense! He moved slowly at first, making me feel his entire length. It felt so good! Knowing that it was my boss inside me made it feel..."

She trailed off once again, searching for the right words.

"Surreal?" Dan suggested.

Matilda gave a slight shrug. "Well, not really. We'd built up to this the past weeks, and now that he finally fucked me, it kind of felt like the natural thing to do. I felt like this was fitting for who I am."

Dan made a single chuckle, making her head against his shoulder bounce. "And who exactly are you?"

Matilda didn't look up to meet his eyes, but her words were resolute as she continued. "Not long ago, I couldn't have imagined doing something like this, but yesterday, I just accepted that I'm the type of woman who thinks it's OK to fuck her boss on a business trip. I feel like single women can fuck whoever they want; married women must limit themselves, but not just to their husbands."

Her own words shocked her. She didn't realize until they left her mouth that this was how she felt. She expected her husband to comment on her newfound point of view, but he said nothing. His silence made her worried, and she sat up straight and looked him straight in the eyes.

"But I know it was only this one time," she added. "I know it sounds crazy, but I felt at the time―and still do, I guess―that it's pretty normal for a married woman to occasionally sleep with her boss. But that doesn't mean I expect you to let me do it again. I'm beyond grateful that you allowed me this one time."

Dan remained hard to read. He didn't appear at all shocked. If anything, he seemed amused by her words.

"Please, continue," he said.

Matilda took a moment to collect herself. Her confusing cocktail of emotions made it difficult to speak.

"It got more intense," she said, picking up where she'd left off. "I was so turned on by the whole thing that I quickly reached... It's a bit of a haze, so it's hard to remember exactly, but I think I asked him if it was OK to cum. He said something like 'yes, come for me, slut,' which pushed me over the edge. He stared down at me, watching as I... God, I came so hard!"

She clenched her legs together as she recalled the sensation of climaxing with George inside her.

"Did he come too?" Dan asked.

Matilda shook her head. "No. I think he wanted to make it last. Once I'd come down from my orgasm, he told me to go down on him again. I loved being ordered around. I thought he wanted to come in my mouth like he did the other day in his office, but he pulled me away before I made him come and told me to get on my hands and knees."

She was flushed by intoxicating memories of holding that position on her boss's bed, yearning to have him inside her again.

"And when he entered me... Oh my god, honey. It's so good!"

She kissed her husband. He had to give her that much. His tongue responded, and she thought that he finally gave in. Yet, to her dismay, he once again pushed her away.

"Tell the rest," he said, speaking through his teeth.

"He kept fucking me, steady and hard. There is just something about being taken from behind―it's primal. I started thinking about what you'd think if you saw me like that, and it wasn't long before I came again. I could hear George was close too, but apparently, he held back once more. Not for long, though..."

Matilda felt her cheeks heat up. At the time, it had felt so perfectly fitting―something she couldn't wait to describe to her husband. Now she hesitated. Did Dan really want to hear the end of this, especially if he'd had a change of heart? She stalled, twirling her hair around her finger.

"Go on," Dan pressed impatiently.

Matilda stared down at the floor. "Well, he wanted to come on my face."

She heard a light gasp from Dan, and she couldn't tell if it was from shock or excitement. When she forced her eyes up to meet his, his expression remained hard to read. Yet, his cock was as hard as ever.

"He told me to kneel on the floor," she continued, adhering to her promise to not hide any details. "I instinctively knew exactly what he wanted and brushed my messy hair from my face and opened my mouth. He must have been very close, and he rushed to aim his dick at my face. As he came, I still felt the aftershocks of my orgasm. And, wow, he came a lot!"

Nervous and excited, she giggled, hiding her face in her palms.

"Was that the end of it?" Dan asked.

Matilda started nodding but realized it wasn't completely true. She must have looked comical when her nod morphed into shaking her head. "Well, it was kind of the end for then―we showered together, and then I stayed with him in his room for the night. I slept naked, partly because I didn't want to go to my room to get something to sleep in and partly because it felt sexy to lie there naked next to my boss. I knew it was a one-off deal, so I wanted to make the most of it―and so did George. I woke up to his hands on me."

She illustrated George's touch by firmly groping her tits.

"When I pressed back against him, I felt his erection poke against me," she continued. "I don't think I was fully awake yet by the time I had it in my mouth. I've sucked his cock enough times lately to know what he likes, and I could easily have finished him off. I was still his to order around for the night, but I stopped before he told me to. I wanted to have him inside me one more time, so I straddled him and started to slide up and down his cock without putting it inside me."

On a whim, she swiftly swung one leg over her husband's lap. She pressed her sex against his. Unlike when her pussy slid naked along George's cock, she had several layers of fabric separating her from Dan. Yet, she could feel how hard he was.

"Please," she whispered as she rubbed against him. "Let me see it."

He grunted, and she reached for his fly, wanting nothing more than to relieve him. He put his hand on hers to stop her.

"Tell the rest of the story first," he said, his voice strained.

'First?' Matilda thought. Didn't that mean he was going to give her what she craved afterward?

"OK," she said, her heart fluttering with hope. She remained straddling him as she continued her story. "I slid his cock inside me and started to ride him. It was hypnotizing to watch his cock repeatedly disappear inside me. George just lay back to watch me, so I put on a bit of a show for him."

Dan cocked his brow. "A show?"

"Not an act or anything. I just didn't hold back anything. I let myself go wild, bouncing on top of him. I even played with myself, but not too much. I didn't want to finish before..."

She paused.

"Before what?" Dan pressed.

"I loved that he came on my face after the first time; it was very fitting for the situation. But I also wanted the experience of climaxing together, so I forced myself not to do it before him. When he signaled that he couldn't hold back much longer, I rode him harder. There is just something special about the way it feels when a guy comes inside me, you know. Sorry, was that too much?"

She hoped it wasn't too obvious when she pressed her sex against his to reassure herself he was still excited by her words.

"Do you mean the act itself, or you telling me about it?" Dan asked, holding her steady by the hips to stop her from dry-humping him. She couldn't if it was because he didn't like it or to stop him from coming in his pants.

"Either, I guess," she said, "but we agreed I had to be open about everything."

Dan smiled at her. "Indeed, that's what we agreed on, and―wow―you certainly held up your end of the deal. That's quite the story―almost hard to believe."

Matilda felt hurt. Was he accusing her of making it all up? Sure, what she'd done might seem inconceivable, given how quickly things had escalated to this. Yet, it seemed unfair.

"Honey..." she said, giving her husband a somber stare. "I wouldn't lie to you. We agreed that giving me a night with my boss could even bring you and me closer, as long as there are no secrets. I still feel that way. Are you having regrets?"

He gave her a bewildered stare, as if what she'd asked was preposterous. "What? I... You think...?"

His face cracked up and he started to laugh.

"What's so funny?" Matilda demanded, not the slightest amused.

Dan collected himself. "Sorry, I just thought it was obvious how I feel."

Holding her by the hips, he pressed her against his erection.

"But maybe you're having mixed feelings?" Matilda suggested. "It wouldn't be so strange after giving your wife such an extraordinary once-in-a-lifetime experience."

He gave her a curious look. "Is that what you want it to be―a one-off thing?"

"Yeah, of course. That's what we agreed on."

"Yes, but is it what you want?"

Matilda climbed out of Dan's lap and rose to her feet, feeling she had to put distance between her aching pussy and his erection to think with her head. What was he implying? Was this a trap?

"Babe..." she began. "I don't know what you're implying here, and, I mean, it was amazing. It was sexy and liberating and... But nothing good could come out of regularly sleeping with my boss, right?"

Dan gave an ambiguous hum. "I've been thinking a lot when you were gone, and I realized I've been selfish."

"How can you say that?" Matilda protested. "You've given me an amazing experience without asking for anything but my honesty."

"Sure, but we both know I enjoyed this too. I can't explain why―even to myself―but I love this side of you. I don't think I am ready to say goodbye to it."

"OK," Matilda said tentatively. "I still don't know what you're suggesting or why you think you've been selfish."

"I was selfish by letting you explore our boundaries on your own, even though you made it obvious from the start that it was the boundaries imposed by your office policy that made you feel safe. I should have given you stricter rules of what I am prepared to let you do."

"What kind of rules?"

"Well, for starters, to keep being honest."

"I am honest," Matilda said, still frustrated by the mere implication that she wasn't.

"Still, I want to make it clear that you can't keep any secrets if we move forward."

"Move forward to what?"

Dan took a deep breath. "I agree that it's probably not a good idea that you'd regularly sleep with your boss, but the other stuff―I see no reason why that can't continue. Again, I can't explain why, but I like the idea of you being felt up around the office, and you're getting turned on by it―it's... Well, I like it."

"I like it too," she admitted. "But I did a lot more than just let him feel me up. Are you really suggesting I should continue with all I've done around the office? I might end up on my knees a lot."

Dan gave her an unwavering stare, letting her see his eyes glowing with excitement. "Yes."

Matilda was taken aback by his candor. It was a stark contrast to the stone-faced vibe she'd picked up on since arriving at home. "Oh, honey... I don't know. And I don't think George wants to continue."

"No? How so?"

"Well, I did the walk of shame back to my hotel room this morning―certainly getting a lot of knowing looks in my evening dress. After getting changed, I met him for breakfast, and we talked as if nothing out of the ordinary had happened. I appreciated it―not because I wanted to pretend last night never happened, but because part of me apparently thinks it's expected that a married woman who goes on business trips with her male boss ends up having sex with him. It's not worth talking about."

She paused, marveling at her own words. How could she feel that way? And how could Dan just nod in agreement?

"We continued chatting like colleagues the entire trip home, including when he drove me home from the airport," she continued. "When we arrived at our house, it occurred to me that my free-card was technically valid for my entire trip, and I casually asked him if he wanted a blowjob in the car before leaving. I guess I wanted to come home and tell you what I'd just done―maybe even show you the evidence."

Dan stared expectantly at her. "Yeah?"

"But he turned me down," Matilda said. "He said I'd better get home to my husband, which I guess was considerate, even if I felt a little rejected. I assume he thinks this has gone far enough."

"But what do you think?"

"I don't know what to say, honey. I guess if you think it would be OK and my boss still wants to... But what are we talking about, exactly? Anything but actually sleeping with him?"

"I said you shouldn't be sleeping with your boss on a regular basis," Dan said. "That doesn't mean you shouldn't ever do it again. It would be strange if you didn't have sex with your boss on your next business trip, right?"

He winked at her. Matilda was stunned, mouth gaping. Eventually, she cleared her throat.

"So, you're essentially telling me I should do anything he wants around the office except going all the way, but if I go out of town with him, anything goes?"

"I'm not saying you should do anything," Dan said. "I'm just giving you my limits. I'm sure there will also be times when you'll want him to fuck you, even if you're not out of town. We can't foresee every possible situation where it would be appropriate, but I must set some boundaries, so you'll simply have to ask me first."

"Appropriate?" she questioned, her cocked brows imploring her husband to elaborate. How could any of this be appropriate? Two weeks ago, it would have been unthinkable that she would ever have sex with anyone but her husband. Was Dan now suggesting she could continue her affair? It seemed insane.