My Wife's Christmas Surprise (Cuckolding Shorts Book 5) (4 page)

Finally, I broke the silence. "Maybe we should get going," I offered tentatively.

"Nonsense," Roger boomed as he reentered the room, clad now in a bathrobe. He’d lost the hat. "We're just getting started, aren't we Jules?"

She looked over at me. I slumped. She looked back at Roger and shrugged amiably, signaling she was game for more. She put down her wine glass

“What do you have in mind?” she asked. 

“That was for you. Now this going to be for me.”

He led back over to the sofa. He maneuvered her flat on her back.

"Now pull your knees to your chest," he directed.

She complied willingly, completely exposing her still swollen and glistening snatch.

"Beautiful, isn't she?" Roger said, more as a statement than a question.

He gently caressed her well-worn pussy, running his fingers over her labia, and sliding a finger down her slit.

“Nothing prettier than a freshly fucked pussy… though it would have been a treat to come inside it. Maybe I’ll be able to give you a creampie next time, huh Jack? That would be a nice Christmas treat.”

Roger continued playing with her swollen snatch. But he didn't stop there. He gently tickled the sensitive skin between her pussy and her anus, and then with excruciating deliberateness he began to trail his finger around the rim of her little, pink pucker.

He turned to me. "Have you ever had the pleasure?"

I shook my head, and croaked out a soft, "no."

"And you, Jules, have you ever had a man in your ass?"

"No," she replied equally softly.

"You sound apprehensive. Does the thought scare you?"

"Yes."

"It should," he replied. "Most men don't know what they are doing. All they can think about is jamming their cock in there. But it's not really about the penetration."

As he spoke, he withdrew a tube of lube from his robe pocket and squirted a gob onto his fingers. He continued to caress her anus, now slowly pressing the tip of his middle finger inside her.

"I get why gay men are like that. Men have a prostate. Getting a dick up in there stimulates it, and they come like a fire hose. Any pain is a small price to pay."

He turned back to me again, "Have you ever taken it up the ass, Jack?"

I tried to think of a snappy comeback, but the sight of his finger now sawing in and out of my wife's butthole was too distracting.

"No, I haven't. It’s not my thing," I explained absurdly.

He grinned and regarded me skeptically.

He went back to his lecture. "Truth is, for straights, anal sex is sort of unpleasant. Often at least a little painful for the woman, no matter how slow you go. Sometimes messy. And truth be told, an ass just doesn't feel as a good as a hot, wet cunt."

He added more lube and worked his thumb into her ass, making Julie grimace and let out soft hisses as she adjusted to the thicker digit.

"So why do it?" He paused in his monologue to add yet a little more lube into the mix as he now began to work two fingers into her. "Well, isn't it obvious? Just look at her. Lovely. Holding herself open for me. Exposed. Vulnerable. It doesn't really matter if it is out of fear or lust or greed or whatever. What makes anal special is submission."

He was now gently, but insistently, finger fucking her ass, both fingers going in past the second knuckle. Julie was now mewling softly at each thrust, lines of tension radiating from her eyes, her mouth tightened, baring her teeth, but still she submitted, holding herself open for him.

"It's time," he said finally to Julie. "Get the camera," he ordered me.

Again, I passively followed orders, positioning myself behind the couch to catch the best angle.

Roger had stripped off his robe. His cock was again rock hard. He quickly coated it with a layer of lube and then approached my wife. He pressed the head of his cock against her puckered anus and applied firm pressure until her sphincter relented and the tip of his member entered her.

Julie gasped loudly, her eyes now tearing up slightly.

"Shhh, baby, it's alright," he whispered comfortingly. "Just breathe and relax."

He began fucking her ass in earnest now, thrusting his cock in and out a fraction of an inch at a time until she adjusted to the intrusion before going in deeper. It was slow going, but he patiently continued to push the envelope, managing her discomfort while relentlessly going deeper, harder, faster. When he was a couple of inches in, he grabbed her ankles.

"I have your legs now. Rub your clit for me."

Julie seemed skeptical, but she did as ordered, gently playing with herself as he continued to work his cock into her bottom. They were moving in harmony now. The harder he fucked her ass, the more vigorously she played with herself. He thrust in deeper, getting more than half his dick into her. She squealed in pain even as she shoved two fingers into her own cunt. He plunged in deeper still, and suddenly he was buried, balls deep, in her ass. She let out a series of shrill yelps, even as she wildly continued to finger fuck her own pussy. And then, amazingly, her pained cries turned into a passionate, throaty growl and her whole body began to convulse in a wild orgasm.

Faced with this wild spasming creature, Roger seemed to lose his composure. He began hammering her ass roughly, sloppily. She whimpered pitifully under his pounding, but mercifully, he was almost done. With a loud gasp, he jerked his cock from her ass and fired several thick ropes of cum across her belly and breasts.

Without missing a beat, he rounded on me. "Clean her up," he commanded.

I looked at him puzzled, then reached for a box of tissues. He slapped it out of my hands.

"No, use your tongue," he said, fixing me with an intense stare.

"I don't want to," I muttered.

"Do it!"

As if under a compulsion I took a step toward Julie. And then suddenly, I got mad.

"No, damn it, Roger. I said no!"

I braced myself for the coming assault, some vicious mixture of physical intimidation and verbal abuse. But it never came.

Instead, Roger let out a loud, rolling belly laugh. I looked up to see him nearly doubled over with mirth. I looked over at Julie and she had her arms raised in triumph.

"Finally," she groaned.

Roger got himself back under control. "Well, it seems like you do have a spine somewhere in there."

She laughed. “It’s a Christmas miracle!”

I looked at him and then her perplexed. "What?"

"I can't believe you let me fuck your wife in the ass. How could you let it go that far?"

I must have still had a clueless look on my face because he continued his explanation: "On the dance floor, Jules was bitching that you never stand up to me. I tried to convince her she was wrong, so I told her, 'watch him come out here and pull me off you.' I figured when I first grabbed her ass, you'd be all over me. But you stood there like a big dummy, so we decided to teach you a lesson.

"Lifting up her dress. Putting my hands inside her panties. Jesus, Jack, what were you thinking?"

I had no answer.

"We figured you might not have realized I was finger fucking her on the dance floor, so we made it unambiguous in the car. And still, nothing."

I suddenly felt almost sick. "Oh God," I muttered. I turned to Julie, "I'm so sorry, can you forgive me?"

She chuckled softly. "Don't apologize to me. Roger may be crazy, but he's a heck of a fuck. I'll repeat this lesson as many times as needed to get it through your thick skull."

I was speechless, trying to process all of it.

After a few moments, Roger leaned over to Julie and gave her a quick kiss on the lips. “Looks like we tore out a few pages from that book of things you won’t do with me.”

She grinned back. “I’m not sure there are any pages left.”

He chuckled. “We just scratched the surface tonight.”

He let that hang in the silence for a few moments. Then he yawned, stood, and started walking to his bedroom. Without looking back, he bid us farewell, "lock up when you leave."

The cab ride back to the nightclub parking to pick up our car passed in silence. Once in our own vehicle, though, I was finally able to speak.

“That was a shitty thing to do,” I grumbled.

My voice was tight with anger and disappointment.

“It was,” she agreed. “You should have stopped it sooner.”

“I meant you,” I snapped.

“I know what you meant,” she replied. “And I suspect most people would agree with you. But truth is, I saved your soul. And you know it.”

“Oh, is that right? If I remember correctly, Gretchen pleads with God to save Faust, she doesn’t fuck the Devil.”

“Yeah, Doctor, but that’s only after she murders her baby, gets her brother killed, and gets sent to prison. My way short-circuits all of that.”

I grumbled.

“What was that, Doc?” she asked.

“How could you do that?”

“How could you just watch?”

“You’re blaming the victim.”

She laughed ruefully. “Only because you found it harder to confront your boss than to watch your wife with another man. Think about it.”

I grumbled again.

“You should have that looked at,” she teased.

“So, you expect me to believe this was just, what, a lesson that got out of hand? You don’t have the hots for Roger?”

“Now
that
is an interesting question.”

“How about an interesting answer?”

“Hmmm. Well, let’s see…. He is handsome. And he does have that bad boy vibe that is, honestly, sort of sexy.”

“So you have thought of him before,” I said.

“This isn’t the first time he’s made a pass at me.”

“When?” I risked a glance over at her.

She rolled her eyes. “Really, Jack?”

I knew what she meant. He was an irrepressible flirt.

“He was just playing around. He… he likes to push people’s buttons.”

She laughed. “My butt is still throbbing from the pounding he gave me, and you’re already making excuses for him again.”

“Am not.”

“Oh, Jack, you really will never learn, will you?”

I grumbled to myself.

***

Back in the office the following Monday, I sought Roger out immediately. I closed his office door behind me and confronted him.

“We need to talk.”

“You know the rules. What happens at the Christmas party stays at the Christmas party.”

“What about what happens back at your place?”

He grinned. “It was a special night.”

“For you.”

“And Julie.” He shrugged. “We had fun. You learned a lesson, and we didn’t even have to summon the Ghost of Christmas Future.”

“And what lesson was that? That you’re a manipulative asshole?”

He bristled slightly, but quickly recovered his equanimity. “I deserve that,” he admitted. “But it was for your own good. And mine.”

“Oh, and what did you get out of it other than screwing my wife?”

“Don’t sell that short. She’s… an
amazing
woman. I’ve wanted to wreck that for years.”

I fumed silently.

He continued, “But, more importantly, I get to stay out of jail.”

“Huh?”

“You can’t enjoy life from behind bars. And I… I don’t have a governor. You know that. That’s why I need you to be honest with me. Keep me just
this
side of the line.”

“You don’t like being told no.”

“Which is why I wanted to reinforce your backbone.”

“You’re insane.”

He laughed. “Maybe. But we’re a good team, you and me. I’m the Id. You’re the Ego. We need each other.”

“I’m not sure I can continue to work with you.”

He nodded. “I’d be sad to lose you.”

“You don’t do sad,” I noted. “It would require too much self-awareness.”

He shrugged, but didn’t reply. And after a moment I realized I was done as well. I turned and walked toward the door.

“Oh, and Jack?” he called.

I stopped. “Yes?”

“Now that I’ve cracked open her backdoor, take advantage of it. You know what I’m saying?”

He was deranged.

“Fuck you Roger. And stay the fuck away from my wife.”

“Sure thing, Jack. And hey, I just sent over a new deal book for you to review. Let me know what you think.”

I opened the door and exited, slamming it behind me. A small, stupid victory, but it felt good.

I walked slowly to my office. My original plan had been to tell Roger to fuck off and storm out. But now I was no longer so sure.

He was deranged, which meant, in a weird way, that he did need me. I realized I was stopped in front of my office. I peered inside. There on my desk was the deal book. How many ethically suspect, legally dubious provisions had he included this time? It was tempting to walk away. Let the fucker end up in prison. And yet…

***

“I thought you were only going in for a few minutes,” Julie said when I returned home.

It was past five and already dark.

“I needed to look over a deal.”

She gave me a knowing smirk. “I knew you wouldn’t be able to quit that man.”

I poured myself a glass of Cabernet and sat at the kitchen table as Julie busied herself with dinner. God, she was a sexy thing, even dressed casually in tight jeans and a sweater.

“He says he needs me.”

“He does. But do you need him?”

I hesitated. I thought of his manic energy. And of our swelling bank account. Working with him was fun and profitable. And scary.

I also thought of him with my wife. Fingering her in the backseat of his luxury sedan. How she’d eagerly sucked his prick and later swallowed his come. The confident way he’d fucked her. And how sexy she’d looked, on her back, legs pulled up, as he firmly pressed his big cock into her tight, virgin ass.

If I could stand up to Roger, I could surely find the courage to ask my wife for what I really wanted for Christmas.

I rose quietly and approached my wife. She was stirring a pot and didn’t notice me until I was right behind her. She startled.

“Jack?”

“I think you still owe me.”

“Yeah?”

“I know what I want for Christmas,” I said.

“I gave you enlightenment. What else could you want?”

I angled my hand down the back of her jeans, inside her panties. My finger wedged between her butt cheeks. She squirmed, but not enough to stop me. I explored deeper, until my fingertip found the sensitive skin of her anus. She stiffened.

“Jack?” she asked apprehensively.

“Yes, Julie?”

“That was like a weird situation, you know?”

“Yup.” I pressed my finger into her tight little ass.

She gasped. “I don’t know about this.”

I laughed. “I do. Now, I do.”

###