Lisa & Paul

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Married couple's sissy cuckold start w/ a trans female twist.
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charmer949
charmer949
574 Followers

*THEIR BACK STORY*

Lisa and Paul have been together for twenty years. They were completely bored with each other: mentally, physically, socially and sexually. They knew they needed something to change.

They both noticed how much they'd get stimulated by flirting with other people. At this stage in their union, the only sexual spark either had was with acquaintances and strangers.

Their solution?

They'd each have a one night stand.

It took months of conversation before they could jointly agree on the boundaries to such a provocative decision: to allow each other to have one night of sex with an acquaintance or a stranger. Deep down, they both believed this plan would spice up their complacent libidos.

After agreeing in principle, there were still lots of details to sort out. They'd set guidelines. They eventually agreed on boundaries they collectively would follow.

They landed on some basic agreements:

Paul gets to choose Lisa's lover; Lisa gets to choose Paul's.

Both expect the choice to be someone thin, fit and attractive.

Paul wants to watch; Lisa does not (but has the right to change her mind).

Both agree to describe to each other their feelings and details of their one night stand.

*PAUL NARRATES*

Recently, I discovered the concept of cuckolding. I've become absolutely obsessed with it. I devoured articles, erotica and videos until my brain was absolutely addicted. I beat off every chance I could get--admittedly every day--to cuckold porn.

I had no idea diving into this rabbit hole would be so hot to me. The cuckolding concept seemed to check all the boxes of my desire to be humiliated sexually. And by learning of the many reasons couples liked cuckolding--that weren't about this submissive humiliation--it gave me a mainstream foundation for approaching my wife about the subject--even though for me it was all about humiliation.

What penetrated my brain into addiction status was the psychological idea that Lisa was the sexual superior in our marriage. And I was failing at meeting her sexual needs (note: we haven't been having sex). Therefore, Lisa needed a stronger more virile male to properly please her sexually, properly fuck her. And I would humiliatingly support and watch.

And this fantasy had my feelings of sexually attractiveness to my wife returning.

I hadn't thought about cuckolding as a version of male submission until recently and there was no unringing of this loud bell. The more porn I watched and read, the more I beat off. I wanted this to happen to...well, to me. To be made to feel inferior. In my mind, only wimpy submissive men would let their wives fuck other men.

And how my heart thumped so hard in my chest thinking about the reality of Lisa actually having sex with another man. What if she really likes it? Then what?!

All these submissive thoughts were tapping into my psyche in places I hadn't thought of. I've always had a sexually submissive need in the bedroom; this one night stand plan would get me cuckolded with sexual humiliation and I'd also get laid.

I recalled how I used to eat Lisa's pussy all the time. She'd sit in a chair and I'd get on my knees and service her. We both used to really love that. Back in those days I used to think that orally servicing her on my knees was acknowledging her as my superior.

In my quest to make her my superior again, I devoured online videos where the cuckold was the submissive wimp husband. This turned me on even more. I REALLY wanted to watch my wife get laid. To see Lisa moan and squirm while some hot guy properly fucked her.

Lisa really likes a colleague of mine named Clarence. He is a very attractive, fit, black guy she said looks like Idris Elba.

He often flirted with her, so it seemed like an easy and natural pick for me to make.

When I mentioned my potential choice for her over wine, she loved it.

When I took Clarence out for beers and eventually mentioned Lisa and our one night plan, he was all in.

"Just to be clear," he queried, "you're asking me to fuck your wife?"

"Uh, yes. Bluntly put, yes. But you should know this only happens if you agree this can't ever be mentioned at work."

"Oh, I can be discreet. But YOU should know, she is going to love my cock. She is going to want it again and again. You might think the plan is a once and done. It won't be. I've been down this couple rabbit hole before and I'll be fucking her again," he laughed while boasting, "whether you are aware of it or not."

Damn. Why did he use the term rabbit hole? I thought to myself.

"Sorry, Clarence. It's a one shot deal." I said meekly, already insecure and wishing I chose someone else.

I tried to assert myself.

"I could select someone else," I said in attempted authority.

"It's too late for that," Clarence countered.

"What is that supposed to mean?"

"Lisa is already texting me. You've already told her it's me. You don't want to let her down now, do you?"

I started to get up in false protest.

"Sit down! Lisa and I are already making plans. And listen dude, I know you want to watch. But guess what? I'm not going to let you. You can sit in the next room and listen to me FUCK her while you imagine what my big cock looks like. And your wife is going to make sounds you've never heard before. I bet you have a tiny penis, too." He said while erupting into loud laughter.

"You're one of those sissy cuckold guys. I know the type. Been there, done that. This isn't my first rodeo. I'll fuck your wife for you. I'll do it for YOU. You did ASK me to, after all."

I felt like Clarence was already cuckolding my brain. I didn't like how quickly I'd lost control, yet my penis was dripping in my panties.

Lisa and Clarence went out the next night. Both were so hot for each other, they didn't see any reason to wait.

I convinced Lisa to let me hide in the closet after parking my car around the block and both of us pretending that I wasn't home.

I waited for hours crimped in an uncomfortable position.

When they finally came home, what happened in front of my very own eyes was nothing like what I fantasized about.

Their sex was nothing like I'd read, imagined or watched in a video.

The sex occurring in our marital bed was not anything I anticipated. Sure, all the prelims were normal: the making out...the stripping off the clothes, but everything after that was crazy.

They had no missionary sex. Zero vanilla sex.

Clarence unexpectedly completely sexually dominated Lisa. And not only did she let him, but she liked it. A lot. Fuck. She loved it.

At work, Clarence always seemed like a nice and chill guy; in our bed he was an aggressive, dominant, superior.

Watching him own Lisa put a pit in my stomach; my gut was tense. Yet, my brain was sparking.

Right from the start, he told Lisa to kneel and suck on his dick.

"Blow me, bitch," were his exact words.

Then he teased her about being a sheltered married woman who needs to have regular submissive sex with a strong dude with a large cock.

He made Lisa suck his balls. Then he told her to make out with his butt hole as he turned around and spread his perfectly firm cheeks. As she willingly got into rimming his sphincter, he held her head in place as a show of his dominance.

She actually reached down and started fingering herself. I wouldn't have ever believed what I was seeing if I wasn't seeing it for myself.

He turned around. His cock was really impressive. Intimidatingly impressive.

Clarence told her to ask him for his cum.

"You need to ask for my load, Leesey. You know you want to swallow, you little neglected, horny slut. Put it in your mouth and suck the cum from my cock."

She licked and sucked on his firm, glistening shaft and bobbed her head on it like it was a skill she performed every day.

"Ask for my cum, Leesey," he continued to taunt.

She was mumbling with his huge cock in her mouth and nodding her head and showing her pleasure by rubbing her clit.

"You're going to swallow, aren't you Leesey?"

There was a weird familiarity in his delivery of this nickname he had for her.

"You've been so sexually neglected, you WANT to swallow. You need to taste that slimy sperm to feel like a woman again."

Apparently, she did. She swallowed and swallowed while vigorously rubbing herself.

"Oh, yes I'm cumming. Here's your reward," Clarence teased.

It was surreal to watch. The idea that my wife was sucking another man's huge cock to an orgasm--which he announced he was having--and there was no trace of sperm to be seen from my closet view. Lisa quaffed every drop. I never saw his load; I only heard about it.

Usually, I am not jealous, but Lisa has never eaten my sperm. She has had it in her mouth. She has even french kissed me until I swallowed, but she never did. Well, not that I know of.

Clarence ordering Lisa to eat his cum both weirdly turned me on and pissed me off. I felt like I was getting dominated at this moment.

Clarence wasn't done. He was going to make sure he fucked my wife. That is what he came for.

He was standing behind her. His impressive girth was thick and his length was sizable even when flaccid. His impressive cock had to be six inches when soft. I wonder how long it is when it's erect?

Now Clarence was pinching, stretching and twisting Lisa's hardening little nipples while he lightly kissed the nape of her neck. She started fingering herself again. He lightly brushed her hand away and replaced it with his. He would rub her clit and stop several times. He wasn't going to let her cum...yet.

He laid her on her stomach on the bed. She looked so ripe and ready with her legs spread and her pussy gaping; it was aching to be entered.

He towered over her as he straddled himself above her.

My heart was thumping hard in my chest; my little penis was rock hard in my panties. My breathing might have been too loud as Clarence looked over his shoulder towards the closet as if he heard something.

I'd been crouched in the same position for so long I felt my leg starting to cramp.

I could only see Clarence's muscular dark skinned butt and dangling balls as he entered her.

Lisa was groaning. She wasn't moaning, she was groaning. Her sounds were very different. Like guttural groans emanating from deep within her diaphragm. I can't recall ever hearing her sounding like this when I used to screw her.

As I watched Clarence's firm round butt raise and lower above Lisa's, I could only imagine how deeply he was penetrating her as he slowly fucked her.

My leg started locking up and I had to suddenly move my position. This turned out to be a plus and a minus. Although it gave me a much better view, I knocked something over which made an unexplained noise emit from the closet.

Clarence didn't seem to react to it, so he must not have heard it over Lisa's loud groans. Whew.

With my repositioning, I got the view I was looking for, but was surprised--maybe even shocked--at what I was seeing.

Clarence's long hard glistening black cock was driving deep into Lisa's asshole! He was fucking her ass while her pussy was all puffy and swollen and periodically gaping as she spread her legs wider.

And she was enjoying it. Actually, loving it!

Each time he pulled out, his long, thick, dark shaft was glistening...shining...glowing...and fucking. Fucking my wife's ass.

Now I was really jealous. Even more weirdly turned on and yet trembling from the realness of it all. I was completely helpless as I was mind-fucked. Cuckolded. Passively submissive to the humiliating event that I agreed to.

Lisa was so into her ass fuck, she was raising her haunches--with wide spread legs--to meet Clarence's down thrusts as if her goal was to maximize the furthest depths his long cock could reach.

He was reaching under her and spreading her pussy really wide open as if to taunt her that she needed a cock in their, too.

Her middle finger was running rapid circles around her clit. Clarence let her masturbate now. They both worked at and wanted his cock in her ass as deep as they both could possibly manage to get it.

Clarence started the taunting sex talk again.

"Does your sissy husband know you're a butt slut? Look at how crazy you are for a cock up your ass!"

From experiences long ago, I could see that Lisa was just about to explode.

"Cum on my cock you married slut! I want to feel your butt hole spasm on cock! Do it bitch! Do it! Cum!"

Lisa didn't disappoint. The swollen puffy inner linings of her stretched pussy expanded so much I could visibly see her contractions from the inside of her vagina.

In all our married years, I'd never seen anything from Lisa like this. She screamed expletives and her body jerked--almost violently--with each wave of her orgasmic spasms. And this went on...and on...and on. Like some kind of contractions record; it seemed like more than thirty seconds.

Clarence kept his slow ass fuck going while Lisa was cumming completely unglued.

FUCKING Clarence wasn't wearing a condom. I guess since he wasn't going to cum in her pussy, neither of them felt it was necessary. He was bare-backing my wife's ass in our marital bed. I was nervous and jealous at how he completely sexually overpowered Lisa and used her body. And my sexually submissive brain was sparking. So much so that I unexpectedly came. I erupted in large spurts from having barely rubbed myself through my satin panties. I didn't realize an occasional stroke through the material would lead to an orgasm. This carelessness produced an embarrassingly huge load that was soaking the front and back of my panties. The orgasm itself started when I wasn't even touching myself. I didn't even know this was possible. I felt like Clarence was fucking me too. Fucking my brain. He was cuckolding me into what he later referred to as a sissy orgasm.

Now it was Clarence's turn; he started cumming.

And, of course, he didn't pull out. Damn. Just the opposite; he actually plunged his massive cock to its deepest point and while holding Lisa's bony ass as HE came. It was like he was trying to impregnate her by shooting his cum so deep into her rectum that his sperm would penetrate her thin inner walls and arrive on the other side.

He just held her there fully embedded. Lisa's sphincter--that was tightly gripping Clarence's cock--could feel the spasms of his shaft.

"Oh my, oh gawd, you're coming!" she announced as if surprised.

Her hand went at her clit again. She returned with her own anal messaging. Clarence could feel HER sphincter pinching down rhythmically on his shaft as Lisa had a second orgasm. He enjoyed how it felt like her butt hole was milking the last drops of his sperm into her ass with its periodic squeezes.

Even though it wasn't nearly as powerful as her first orgasm, it was impressive that she was so turned on by his, that she could climax again that soon.

When Clarence got up to use the bathroom, he suddenly changed course to the closet and swiftly opened the partitioned door.

"Did you enjoy the show?" he asked while looking down at my soaked panties. "Well, well. Clearly you did."

It all happened so fast I was paralyzed to react.

His long, glistening--yet softening--dark cock was eye level and just inches from my face. I couldn't help but stare at it.

"Open your mouth, sissy."

"What?"

Everything was happening so fast I couldn't process what was happening. I wasn't even sure if Lisa was aware.

"We both know you want this. Open your mouth."

I was afraid to look up. And in my crouched down with cum soaked satin panties position--which were a clear indication of my somehow twisted enjoyment--I felt I was in no position to argue.

But I didn't want this.

Well, I thought I didn't.

But I wasn't in control of the situation or even myself. So, I opened my mouth.

Clarence laughed and walked away. He went to the bathroom. He got what he wanted without having to do anything. He got me to admit I would suck his cock.

*LISA NARRATES*

When I searched for Paul's one-nighter, my best friend Susan conceived a wicked idea that I agreed could be the perfect fit. He would never expect the date I'd choose for him. But it would be his best fuck ever.

Here is some background for context.

My girlfriends call my husband Polly; he thinks they are saying Paulie. They're not. They've seen the waistbands of the women's panties he wears poking over the top of his jeans. He doesn't know, because I haven't told him; he'd be mortified. They think he might be a late blooming homosexual (or at least bisexual); they know he has lost all interest in having sex with me. And I'm a hot, fit attractive gal.

My best friend Susan so liked her wicked 'test-the-waters' idea, she'd secure Polly's date. She convinced me that this was the best thing for him. With Susan's help, I would choose a trans woman for Polly's one-nighter. She would be hot and she would provide data about Paul's interest in cock.

On Friday, he and I went for beers to discuss my pick for him. He was completely unaware that his night was upon him; that his date was already inside. We've been to the Pink Pony bar before. Paul does know that it's thought of as a gay bar, but he thought we were just imbibing, so he didn't think twice about it while we stood in line to get in.

As we settled into a booth with two pints, Paul was just about to speak when I told him that an acquaintance of mine that 'he might like' said she was coming here tonight.

I described her: skinny, tall, silky long auburn hair, slight, almost flat chest and a small butt. These features, by the way, almost perfectly describe me. Paul has a thing for small butts and tiny breasts on a fit frame...at least he used to.

And before I said another word, there she was. Standing there in all her beauty. She was gorgeous.

"Hi! Lisa?! And you must be Paul. Fuck, Lisa! He IS cute! I can't believe you're gonna let me fuck him! Hi, Paul, I'm Kira!" She spoke with bursting enthusiasm.

Well...so much for prelims. She was so stunning and so perfectly dressed in her see-through tank top sans bra, bare midriff and tight low cut jeans that I could see Paul's initial attraction as he shifted his sitting position in our booth. Could he be getting a hard on?

She must've been tucking as there was no sign of male plumbing in her crotch. Her smooth flat chest was the only hint of the body she was born into, but her puffy feminine nipples--that were so clearly visible through her tank top--loudly announced her sexy female confidence.

Kira took over from the minute she arrived. As she sat in the booth across from Paul she slowly ran her high-heeled foot up his leg to his crotch. Paul choked on his beer from her touch and clutched his ice water. As he attempted to clear his throat, he was so nervous, he swallowed an ice cube.

"Why are your pants so slippery? Are you one of those girly guys who likes to wear panties under their business suits?" She was already teasing him.

Kira was perfectly aggressive, gorgeous, witty and fun.

Paul was now blushing beet red. And started choking again.

"Oops, I see I touched a soft spot. Sorry. Oooh, eee, hee hee. I meant a hardening soft spot!"

Kira was already rubbing Paul's dick with her foot under the table. He seemed to be melting under her direction.

"Come on, Paulie," she coached, "let's get outta this dive bar. You okay if I call you Paulie? Rocky is my all time favorite movie."

Kira was chatting and directing quickly and swiftly.

"...uh...sure...I..." he was overwhelmed by her. He could barely speak.

When he stood up, he could see Kira was several inches taller than him. With her stilettos on, she was an intimidating one foot taller.

She was already dominating him with her personality and presence.

"Oh, you'll do just nicely," she said, looking at and swatting his butt.

charmer949
charmer949
574 Followers
12