Friday, December 27, 2019

Flirt

Just to get this out of the way, she didn't sleep with him on her second date.

Not because she didn't want to, I think she did, does.

Not because he didn't want to; he does, very much, told her so before dinner.

And apparently, while he's nice, he isn't that nice.

Adapted from Emily's retelling:

**********

"I never fucked someone's wife before," Emily said he told her in the elevator up to the restaurant, after they'd dropped off their coats.

"What...what makes you think you're going to?" she asked, taken aback by his directness.

"I suppose the assumption married women don't dress like that when they have dinner with someone they are not married to unless they are trying to seduce them."

"Brian," Emily blushed, feeling the thrill of the situation, turned on recognizing the immediate sexual tension, the hint of danger. "I...before we..."

He stopped the elevator, apparently familiar enough with the restaurant to know the stop button wouldn't cause a piercing alarm. "Let's get something out of the way before we go up, shall we?"

"W...what?" she asked, looking around, suddenly worried he was going to do something then and there in the elevator, not quite ready, not sure if she'd gotten in over her head.

He took a step towards her, she backed up towards the wall; he leaned towards her, she felt the wall, felt herself breathing. "We're not fucking tonight."

"What?" Emily asked, immediately disoriented.

"As sexy as you look, that's clearly on your mind, but not tonight."

"Clear...clearly on my mind?" she asked, still confused.

"I appreciate it," he said, "the short dress and especially the nylons." He put a hand on her thigh, just below the hem of the dress. "Don't think I don't want, Emily, I mean, those legs, this ass." He moved his hand up, grabbed her ass.

"W...why not? she said she whispered, suddenly wanting what a minute ago she didn't want.

"Suppose before I fuck a married woman, I want to understand what I'm getting into."

He started the elevator again, leaving Emily shaking, confused, turned on.

**********

She said dinner was a blur, not the way she expected. He would touch her, on her arm, on her leg, he would tease her, even toy with her.

When the waiter was gathering the bill, he told her, in front of the waiter, part of him wanted to take across the street and get a room for the night.

"What...what did you say?" I asked her when she was telling me.

"What...what's stopping you," Emily asked.

"I'm not sure," he looked at her. "Something tells me you're not ready for that, either."

"I...I'm not...I mean I am...just..."

"This relationship, with...Matthew...how did that work...with your husband?"

"They are very different," she told him.

"Wasn't he worried? Your husband?"

"It's hard to explain," she said, "Matthew never wanted...I mean...it wasn't just sex but...he never wanted...we learned how to give everyone a place."

"You said you were drawn to strong men, I'm assuming your husband doesn't get described that way?"

"N...no," she said, "he's...he's not like that."

"I'm not naive, Emily," he told her, "by strong you mean dominant, right? What's the phrase? An alpha male?"

"I...I don't know," she blushed.

"There's a whole lot written on the web about it. Women want sex with strong men, but often settle down with providers."

"It...it's more than that," she said without elaborating.

"The thing on the elevator," he said, "that's the kind of thing, isn't it?"

"Kind...kind of," she said.

"Sex without commitment?"

"We were...I mean...I don't sleep around..."

"Not what I meant," he said, "sex without the commitment of a relationship."

"I don't sleep around," she defended herself.

"I didn't way you did. Matthew got sex without the emotional commitment of a relationship."

"In a way, yes."

He laughed.

"What?" she asked.

"I assume your husband has the opposite...no, no need to answer that. Listen, if you were single, we'd be across the street in a hotel room already."

"This...this isn't for you?" she asked, feeling disappointed.

"I didn't say that, Emily, I didn't say that at all. It's just something I have to think about, that's all."

In the elevator on the way down, he stopped it again, turned to her. "Were you really ready to fuck tonight? Be honest."

Emily said she had the sense her answer was important but not sure why, not sure what answer he wanted, so decided to be honest. "N...no," she said, sure that was that.

"But you dressed like that anyway?"

"What...what can I say?" she said, blushing, "I'm kind of a tease."

"Turn around," he said.

"Turn around?"

He grabbed her shoulders, spun her towards the wall, pushed gently, but hard enough she put her hands out to catch herself. He put a hand on her ass, over her dress, whispered in her ear. "If we ever do this, Emily, you may regret that."

**********

When they were waiting for Emily's Uber, he leaned towards her. "Strong like that?"

"What?" she asked.

"You like men strong like that?"

"Y...yea," she said.

"Listen, I have holiday obligations with my daughter, let's talk after the first of the year, okay?"

"I...I'd like that," she said.

"No promises."

"Me either," she said.

As the car pulled up, he asked her one last question. "You sure he's okay with this?"

"My...my husband?"

He nodded.

"More than you can imagine."










Monday, December 23, 2019

Second Date


Emily was sitting on the bed lacing her ankle strap heel around her ankle when I walked into the bedroom, my own heels clicking on the wood floor. 

"I...I can help with that," I said in a soft voice.

She looked up at me, smiled. "I suppose that's what a lady's maid is for, isn't it?"

"I suppose so," I said, glad I'd decided on a satin maid's uniform. I walked to her, carefully bent down, felt the familiar tug of garter straps on my stockings. I took her foot in my hands, touched her nylons as I did, finished the heel. Before I stood, I looked at her thigh, the hem of the dress, nodded. "You...you made the right choice," I said.

"It was either pantyhose or a longer dress," she said.

"I think...I think he'll appreciate the dress," I said.

"I still think it's almost too short," she said standing, looking at herself in the mirror. "It's only a second date."

"It's not the usual kind of second date," I reminded her.

"No, I suppose it's not," she said. "Well, it's the holiday season, lots of married women dress up for a nice dinner date."

"Usually with their husbands," I said not meaning it the way it sounded.

"Sweetie," she looked concerned.

"No, Em, I...I didn't mean it like that."

"Are you sure?" she asked.

"As...as sure as a sissy can be," I said.

"I'm not sleeping with him tonight, I made that promise," she said.

"Part of me wishes you were," I said, "this...you know how this is."

"I know...it's not that I don't want to...god I want to...I just feel like...I need another date with him."

"You're not sure?"

"It's been awhile, hon, I just want to make sure. If I was single, I'd be sure, but there's someone else to consider."

"I know," I said, loving her all that much more.

"He...he's going to want to," I said looking her up and down.

"Guess he won't be the only one," she smiled. "Of course, he's got better short term prospects than someone else."

"Em, I..."

"I won't be home early," she said, "but it won't be too late, either." She kissed me softly, careful not to smudge her lips. "You'll wait up?"

"Of course," I said.

"I'll need it," she said, smiled. "Not that," she looked down, "this." She reached up, touched my lips.

"The reservations are for eight," I looked at a clock, "you...you should get going."

"I already have an uber coming," she smiled.

Watching


You're sitting at the hotel bar, watching her, your wife, she's in your direct line of sight, sitting at a table for two, all alone. She's wearing a tight, white blouse, a short black leather skirt, dark hose, black leather boots.

How long will it take? How long until a man approaches her, sits down, across from her, tries to seduce her.

If she was at the bar, it would minutes, maybe seconds. But because she's at a table, some men will be unsure. They typical guys will be too intimidated to approach a woman like her sitting alone.

She knows whoever does approach will be atypical, the most confident of men, the most masculine of men, the type of guy the most opposite from you.

Yet he won't be the man she goes home with.

No, she''s harder to get than that. She'll tell the first man that sits that she's waiting to meet someone and he'll apologize and leave.

The second might do the same.

It's the man that doesn't get up, that tells her in response, "well he's not here and I am" that she'll finally flirt with.

It's this man, this type of man she's waiting for. Not just an alpha man, but the most alpha of alphas.

It's this man she'll take out the hotel room key for, slide it across the table, and tell him to meet her upstairs in ten minutes.

"What about whoever you were waiting for?" he'll ask.

She'll look around the bar, look directly at you, and tell him, "like you said, you're here and he's not," and get up and leave.

It's this ten minutes that make your penis swell in the cage, the ten minutes he's just sitting there finishing his drink.

Wedding Night


"What...what are you doing in here?" he asked, seeing his bride in his hotel room a few hours before the wedding.

"Typical," she shook her head with a sly smile. "Beautiful woman is in your hotel room and your nervous as a school boy."

"No, I mean...it's bad luck to see the bride before the wedding."

"Ordinarily I'd agree," she said, "but since you won't see me after the wedding I thought you'd like to see what you're missing on your wedding night."

"I thought...I assumed...I mean...we have the room," he waived around, "what time is he...won't we come back here?"

"No, sweetie," she said, "you'll come back here and get our things ready for our flight in the morning, he's taking me up to the honeymoon suite."

"I...I thought that was booked," he said.

"It was, it is, he booked it for us."

He frowned, felt the familiar sting of jealousy. "Lauren..."

"It's my wedding night, sweetie, you know I'm spending it with him, not with you."




Changes


"Honey, I know we talked about starting with a month," she started to say, looking at her husband's locked chastity cage.

"And it's been a month," he interrupted, eager for her to get the key.

"Yea, but..."

"You didn't lose the key, did you?" he asked, panic creeping into his voice.

"What? No, of course not," she said.

"What then?"

"I don't know...I...I guess I've kind of gotten used to it."

"U...used to it?" he swallowed, feeling his stomach flip.

"Every day you wear it, you're more attentive than the last, more responsive, more supportive."

"Of course," he said.

"I just don't want a setback."

"Setback?" he asked.

"I don't want to start over...I like this new you."

"But...but Monica, I haven't...you know...it's been a month."

She giggled.

"What?"

"It's like good red wine, the longer the bottle's kept corked, the better it will be."

"But..."

"Let's do this," she said, "let's go another month and see how it goes."

"Another month without sex?" he said, "Monica!"

"I didn't say no sex," she said with a shy smile, spreading her legs, "just no fucking."

"But..." he stammered, looking at her panty covered pussy.

"You don't want to lick me?" she teased, knowing he did, knowing he would.


Tuesday, December 17, 2019

Before



She looks over at you, sees the look in your eyes, knows the doubt you're suddenly feeling. But it's too late.

The time for second thoughts was yesterday, even that morning, before he was there, before your wife dressed in her pretty lingerie, before she was in bed with him, before he started seducing her. 

Before. Before.


Tuesday, December 10, 2019

First Time


"I...I'm scared," I said to my wife as I took her lover's cock in my hand.

"Shhhh, it's okay," she said reassuringly, "just like we practiced on my dildo, stroke it up and down with your hand then carefully take it in your mouth." 

Thursday, December 5, 2019

Dramatic


"I never let you orgasm? Really, that's what you're going with."

"Like...like almost never."

"Pffff," she snorted. "You're being overdramatic; you've already had three orgasm this year, the last one in July. Three. That's one a quarter, for crying out loud."

"But..."

"Three orgasms. Three. I don't want to hear you complaining for the rest of 2019 and for a good part of 2020."


Wednesday, December 4, 2019

Miscommunication

I was sitting, waiting anxiously, nervously. I felt my penis twitching, swelling to the confines of the small, locked cage, anticipating the feeling of being unlocked, of growing, of release.

It had been months since the cage was last unlocked, months since I'd had an erection, months since I'd had an orgasm. While I was milked on the first of every month, ironically that provided no satisfaction, if anything made things worse.

Knowing my wife would be home from work soon (late, it was almost 9, but soon), I went to a mirror, lifted the hem of my uniform to check if everything was proper.


Cage secure and locked. Check.

Stockings even and straight. Check.

Makeup proper. Check.

Uniform complete. Gloves. Dammit. Gloves.

She was working late as her boss needed her to help finish a project. 

That and he wanted to fuck her.

We'd been concerned about it, about my wife getting involved with someone at work, especially someone she reported to. But besides that, he was the perfect lover in every way, happy and eager not just to fuck a married woman, but to cuckold her husband as well.

Her Snap Chat messages from earlier left my brain spinning.

"I asked him," the first said.

"And?" I typed back, fingers shaking.

"He said if you do everything on the list, you get to cum."

Months and months. The first few, at least the key was home. The last month it was at work, in his top desk drawer. It was his decision now, not hers. My release was his control, not hers.

I checked the bullet list for the tenth time.

  • Proper attire
  • Proper hair and makeup
  • All laundry folded and put away
  • Dishes put away
  • Beds changed and made
  • House dusted
  • Nothing out of place

I scanned the list, scanned the house. Perfect. Everything was perfect.

I swear I was going to burst when I heard the garage door.

"God, you're waiting like an anxious puppy," she laughed when she walked in the door.

"It...please," I said, unable to properly form words.

"Let me look around," she said, inspecting the house, me. "Looks good," she finally said.

I swallowed, hard, looked down between my legs.

"What?" she asked, a puzzled look on her face.

"The...the key," I croaked, barely able to talk.

"Key?"

"To...to the cage," I said dizzy with excitement.

"It's in his top desk drawer, where he always keeps it," she answered in a strange voice.

"But...but I...I mean...how...how are you supposed to unlock me."

"Unlock you?

"You said...you said he said...if I...if I did everything...if I did everything I got to cum."

She laughed.

"What?"

"You need to read your chat's closer, hon, he said if you did everything, you got cum...not 'to cum'.

"What?" I asked again.

"Cum...no 'to' just cum. My god, you thought..." she laughed, shook her head. "You  thought he'd let me take the key just because you behaved? Sweetie...."

"But..."

"You got cum," she said softly, "his cum."

"But..."

"Get my dildo," she said, en evil look in her eyes.

"You...your dildo?"

"The second time he did it inside me so you can lick me clean. But the first time he did it in a condom so I could bring it home and...you know...with the dildo."

My heart sank but my penis was absolutely throbbing. I didn't get to get unlocked, grow, and cum, I got to lick her boss/lover's cum from my wife and lick even more from her dildo, like I was sucking cock.

"He's going to find this funny," she smiled.

"You, too?"

"Not funny," she said, expression changing. "I know it's been awhile, but you know his rules."

"I thought...I just thought..."

"A chastized cuck is a happy cuck," she said mimicking his voice. 

"But..."

"Come on, you know how hot I get watching you suck his cum from my dildo."