An Escort's Chastity Cuckold Ch. 03

Chapter 3: West-side Incall

1. jerry

It had been the best night of his life. Dahlia and jerry had been making Love with Her cock so often and so intensely that this was sex for jerry now. he knew every vein and ridge of Her cock; as it slipped or was forcefully rammed in his ass. he could recognize Dahlia's moans and mewls. She came while fucking him, typically 3-4 times at least when She takes him. And She always cums most explosively and loudly when Her cock makes Her bitch cum for the first time of the session; the 2 Lovers feel their souls unite as they cum together so explosively. Usually Dahlia keeps going, pushing out 4-6 orgasms out of Her bitch's cunt.

Somehow jerry was able to rise with his alarm at 6am, of course Dahlia showered with him. She loved washing Her bitch, especially his caged 'clittie' and his well fucked cunt. Of course, jerry loved anytime he could wash and caress the Gorgeous courtesan. Dahlia had jerry put on Her dirty panties from the day before, and drizzled the cum of another condom She produced from Her bag on jerry's caged 'clittie' then let the panties 'snap' in place. The cum would quickly dry and the crusty feeling would be with jerry all day.

The Lovers kissed passionately at the door jerry saying, "should be about the same time tonight, Love."

Dahlia fiercely and possessively grabs the chastity cage through jerry's pants. "Sounds great babe. Btw, you should know, you're the only man I fuck in the ass now. Our intimacy and love-making means so much to Me, I don't want to share it."

jerry is dumbstuck, "fuck Dahlia, i Love You too, i had no idea." Not wanting Dahlia to lose potential clients and understanding that guys would love to be pegged by a Goddess like his Girlfiend, "we can discuss this later, but do You think that this could be a great way to bring Your submissive clients into Your cuckold sessions? As i have to watch another man take Your cock that represents how we make love making me Your 'pegging-cuckold'?"

Dahlia beamed at the idea, "Damn jerry, you need to go to work right now or I'm going to tear your clothes off and pound that cunt for hours. That is a GREAT idea, I am so HOT thinking about it. Now go," She says pushing me out the door and swatting me on the butt. "while you still can cute ass bitch of Mine."

2. Dahlia

She thought to Herself, 'damn, She knew She was taking a risk putting Herself out there and claiming jerry. But he was a pretty smart and cunning little bitch. This pegging-cuckold idea was inspired.' Her twitter ad had rapidly filled Her DM's. She filtered them down to half dozen or so that seemed serious. One guy said he'd heard about something called a 'cuckold-session' Dahlia replied that She's only offering that on weekends, but then added; actually, if you want to schedule for 4PM then we can do it, you appreciate there is an extra fee for this session right?"

"yes, of course; but I've always wanted to fuck a hot chick in front of Her cuck. And My friend Paul highly recommended the session."

The first guy came by at 9am, parked in spot 'H' as instructed, Dahlia watched him through the window, Asian guy; this was tech country. She answered the door after a couple of knocks wearing a shimmering blue cocktail dress that ended just below Her butt, and had a plunging 'V' neckline that left Her considerable assets on full display. Of course, Her make-up was perfect, She looked like the high-class escort She was. Her gentleman caller's mouth hung open.

"Greg, isn't it?" Dahlia asks as She warmly welcomes him with a sensual hug.

"yes," Greg manages to stammer out, "my Gods You are Gorgeous Dahlia, I've been following You for some time, but could never get out to the East-side to see You, I should have found a way. Is this Your new place? Can I hope to be able to see You here regularly?"

"Here take a seat on the sofa while I get us some wine so we can talk for a bit." A few minutes later the sexy escort returns with 2 glasses of red wine She offers one to Greg. To answer your questions, yes and no. This apartment is actually My boyfriend's; he's at work right now."

Greg is a little taken aback by Dahlia's frank admission, "he knows You're an escort, and is OK with it?"

Dahlia smiles broadly; showing off Her perfect teeth so perfectly set off by Her bright red lipstick, "oh definitely, he wasn't afraid to come to the East-side a few weeks ago and see Me. We clicked amazingly well; I decided I had to have him. I invited him to a movie and dinner, I took him back to My place, locked him in chastity, and fucked him in the ass."

"So, he's OK with You escorting still now that you two are dating?" Greg asks incredulous, kicking himself for not going to see Dahlia on the East-side."

"Obviously," Dahlia says fingering the key between Her breasts, "remember he's locked in chastity, we make love with My 12-inch strap-on cock. And we make love all the time! I also offer a special session now for clients where he's there to watch Me get fucked."

"Wow," is all Greg can say, it sounded like a dream.

"But," Dahlia says as She rubs Gregs inner thigh and looks into his eyes sensually until their lips meet. "enough about My cuck for now Hon." She rises and takes his hand, "how about you go fuck me on his bed?"

Greg eagerly followed along, he was so turned on, his cock was rock hard hearing about Dahlia and Her cuck. It proved to be too much for him, Dahlia helped him out of his clothes and seductively removed Her dress, She slipped the condom on him with Her mouth which Greg was barely about to contain himself. But when She sank her sweet pussy down on it, he blew.

"I'm sorry... SOOO sorry Dahlia. I was so excited." Greg stammered, disappointed in himself.

"Sweetie," Dahlia reassured, "don't worry about it, it's your dollar. And who says I'm done with you already?" She removed the condom, tied it off and set it aside, "for My cuckie." She told Greg with an impish grin. "speaking of, could you help Me get a few treats for My chastity cuckold? he doesn't know I'm hosting in his apartment; he'll LOVE it!"

Greg smiled, "of course Dahlia, always happy to help a Gorgeous Woman like You."

"Here," Dahlia says handing Greg Her phone, take pictures of Me sucking your cock, be sure to get parts of his bedroom in the background, it'll make his little dick so excited in its tiny cage."

3. jerry

it was difficult to concentrate at work knowing that a Goddess was waiting for him at home. on cloud nine as he'd never had a raunchier or more satisfying sex-life. But it was more than that. the emotional connection he felt to Dahlia. She was everything to him, all he could think about, he realized that he no longer cared about his dick in chastity. The pegging-cuckold idea was his, but he was wondering how he would really handle seeing the Woman he loved so deeply pounding some other guy in the ass. that was how he and Dahlia made love! it was his idea, he needed to come to terms with it.

Now he worried that Dahlia would be bored in the apartment all day, there were movies and lots of streaming options. But not much to do.

Bleep... a text from Dahlia, "thinking of you cuck!" along with a picture of Dahlia's pretty face sucking a cock on his bed with his nightstand clearly visible.

jerry went to the bathroom to wash his face and process.

It made sense, jerry knew it did; and he could feel his cock fail to harden in its micro-chastity cage; well, as much as it could in the tiny micro-chastity cage.

Texting back, "obviously Goddess. glad You found something to do. Let me guess, 'West-side incall?'"

Bleep... another text from Dahlia, "damn babe, did you see My tweet?" along with a picture of Her riding some Asian guys' cock"

Smiling jerry sends back, "tweet? No. i just know how my Goddess's Gorgeous mind works" jerry would swear that his cock was testing the tensile strength of the Steele that contained it he was so turned on. As the day went on;it seemed impossibly long with Dahlia sending pics of Her with another cock every hour or two he did a few mental calculations, presuming $400 sessions, and he counted at least 5 different guys. She made good money today.

The day dragged on. Finally, 4:00 came and jerry raced to his car; he couldn't wait to get home. just knowing that Dahlia was going to be on fire and fuck his ass with a ferocity that he was amped for.

4. Dahlia

She was glad that She was able to help Greg recover and go again, She suspected he was submissive and envied Her cuckold. Should be able to help him once She worked out the scenario with Her bitch; She did want to pound that tight Asian ass.

Her other dates went pretty much the same way, all Her clients were Wowed by Her relationship with jerry. She could tell which guys wanted to be in his place. She'd remember them, a couple guys wanted to be Bulls. Only one thought it was weird and just wanted sex and go.

Then Her 4:00 arrived. Michael was tall, at least 6'6"; well built, and wore a suit! Dahlia always re-applied Her make-up and blue dress between clients. She was dwarfed by Michael. But She knew they looked like a perfectly matched couple next to one another. She managed to get a picture of them as the handsome couple they made.

She sent it to jerry, "Michael and I will be in the bedroom when you get home cuck. Strip down to your chastity and come in."

Dahlia was excited, this was going to be Her best lay all day. Michael was so handsome and well-built She needed him inside Her. in the bedroom, on the bed She wastes no time getting his pants off. She isn't disappointed, his cock had to be at least 11 inches and thick. She took him deep into Her mouth and down Her throat. She looked up at him, a look of raw need on her face.

"Your cuck due home at 4:30 Babe? We'll be able to hear when he gets home?"

"Yes," Dahlia answers with a devious smile, She knew what Michael had in mind. "let's start fucking around 4:25; We can kick it in when We hear him come in? I'm sure he'll be a disobedient little cuck and listen at the door for a few minutes before coming in. I'll have fun penalizing him for that." She pronounced with an evil grin.

With the plan set the pair waited on the bed making out and groping one-another passionately. Finally, at 4:24 Dahlia gets in doggie position facing and at the end of the bed.

When Michael enters Her She gasps and utters a satisfied, "finally" She knows already it's going to be hard to wait until jerry is home and listening to cum. But She could enjoy Michael's big cock until then.

At 4:27 They hear the front door open and close, Michael kicks it in and really starts fucking Dahlia. Dahlia gives over to Her desire and screams impossibly loud, "OOHHHHH fuck, yes!!! Yes! Yes! Your cock is so fucking big."

"yes Whore, it is." Michael says playing it up, "bigger than Your pathetic boyfriend whose bed I'm fucking You on?"

"OH yes Sir." Dahlia says taking Her queue; knowing that Her submissive, deferential tone will trigger further inadequacy in Her cuck.

5. jerry

jerry knows he was told to undress and come right in, but he just waited for a few minutes listening after stripping.

He was stunned to hear his Goddess call another man 'Sir'; She was above all. She had caged his cock and claimed his ass and him because She chose to. She reported to no one!

"he paid for a date with Me several weeks ago," he could hear his Love telling a stranger, "his tongue was good, his cock laughable. But it was his submissive streak that caught My eye."

Just then jerry opened the door. "it's about time cuck." Dahlia says in an annoyed, stern tone. "get over here."

Meekly jerry walks to the end of his bed where Dahlia's face is. Michael is fucking Her, hard. "Oh, fuck Michael, that feels great Sir!" and Dahlia reaches out and squeezes Her cuck's nuts with Her right hand; HARD!

"OWWW Goddess, that REALLY hurts," jerry cries out.

"Good!" Dahlia says, clearly pissed. She doesn't let up, simply asks Michael to let Her know when 3 minutes have passed on the clock, "it's supposed to hurt. you disobeyed Me slave, I told you to come straight in. so I'm going to keep squeezing My balls here for 3 minutes to remind you to obey next time."

Meanwhile Michael starts using long, deep thrusts of his massive cock so that Dahlia's cuck can see him fucking what he can never have. "So, Babe," Michael says resuming their prior conversation, "as You were saying You actually let him put that thing inside of You once?" gesturing to the cuck's micro-chastity caged cock. And laughing.

"Ohhhhh, ohhh, OHHH fuck Sir that feels amazing!" Dahlia cries out. "Occupational hazard You know, I don't get to be choosy, his was certainly not the smallest I've had, though I suspect it soon will be after a year or two in that micro-chastity cage. I've read that the smaller cages shrink dicks into clit-sized nubbins. I'll watch the progress, if it's not fast enough I'll have to down-size to a flat-cage, maybe even an inverted to push the little guy in."

Hearing Dahlia talk of this for the first-time jerry cries a little not just from the iron grip on his nuts, 'what did She want to turn him into?' he did not care; he knew he would become whatever his Goddess asked him to.

"Oh yeah," Michael says with a chuckle, "it's been 7 minutes"

"Ohhhhhhh, ahhhhhh, Oh My God!" Dahlia screams as a powerful orgasm overcomes Her causing Her to grip down even hard on jerry's hapless balls. Causing jerry to scream in agony

Dahlia's laughter wakes him out of his pain induced stupor. Was She laughing because Michael had missed the mark by 4 minutes or just because of his pain, jerry didn't know. So, he asked, "Goddess Dahlia, i am so glad to see You again, so sorry for my dawdling about coming into the room, but i have to know why were You laughing so hard just now? Michael's extending Your punishment by 4 minutes, or my pain? i must know, i love Your laugh, want to elicit this again and again."

Michael is still fucking the Blonde btw, a little slower and steadier for now, Dahlia laughs again, "both My dear bitch." She says pulling Her boyfriend in for a deep kiss while another/real man continues fucking Her. Dahlia laughs again, "Both, and the fact that when I gripped down on those useless nuts so tight as I came so hard from Michael's cock. Also, being honest, the pain I was causing you I apparently squeezed cum out of the balls through your little caged clittie there."

Everyone looked down at jerry's caged member, indeed there was a significant amount of cum that had oozed out of it.

Michael and Dahlia both erupted in laughter, even jerry chuckled a little.

"BTW dear, you no longer have a cock, we're going to call it a 'clittie' from now on." Dahlia pronounces authoritatively. "Now Michael, You big stud, Your cock is amazing, but You haven't cum yet. What can we do to make that happen? I'm sure my bitch is eager for us to make-love; which You said You wanted to watch."

"Ah yes, cumming. I'm supposed to do that." Michael chuckles, "all of this has been helping Me get in the headspace I need, but let's switch positions. I'll lay down and You mount Me in reverse cowgirl. It'll give Your cuck a great view of the pussy it can't have while My cock fills it over and over again."

Reluctantly Michael leaves Dahlia's pussy to change positions. As Dahlia sinks down on Michael's cock again this time facing jerry, the sheen of sweat on Her luscious body evident, the key to his chastity sparkling in it.

Dahlia realized that another advantage to this position was that She had control, She could ride the massive member much harder, faster and deeper than Michael had been fucking Her.

"Oh, OH, ohhhh, oh YES!!!" Dahlia screamed as She was cumming almost constantly now, She just wished She had jerry's balls in Her grip again.

For his part jerry was transfixed watching the pussy he adored, but couldn't have, glide up and down around the massive shaft. Dahlia Herself was in Her Glorious element, She was Gorgeous, glistening in sweat as She rode as orgasm after orgasm overcame Her tight frame. She was looking at him, beckoning him. jerry went to Her, She pulled him into a deep kiss with one hand, while the other gripped his balls again. HARD as She came again. Michael finally came with a satisfied roar and Dahlia could feel the XL Magnum inside Her filling with cum; and sure, enough so did jerry. A little more aware this time is screams were of pleasure and pain.

For 20 minutes the trio just lay together on jerry's bed bodies quivering for a while as the aftershocks of their orgasms subsided.

It was jerry who recovered first. Trepidatiously asking, "can You make love to me now Goddess?"

Both Michael and Dahlia erupt with laughter, Dahlia responds, "of course bitch, fetch Me My cock. Michael, You're welcome to watch participate if You have more in You."

"Oh, I'm sure Your bitch would love to help Me in that department." Michael suggests as He moves into position over the cuck.

Stepping into Her harness Dahlia says, "of course he will. Won't you bitch? get in position on the bed."

"ohhh yes," jerry moans softly as Dahlia's big cock slides into him. he's eagerly sucking on Michael's cock trying to make him hard again. Dahlia is really laying it into Her bitch with long deep strokes by the time Michael is fully erect.

"Say Babe," Michael starts, "I wouldn't mind trading holes."

jerry's eyes go wide!

But his Owner saved him from that humiliation, at least for now, "Sorry Dear," Dahlia says as she really starts hammering Her bitch hard and deep. "I am always of a mind to please My customers, but this cunt is exclusively Mine. at some point I'll probably share it; but that's well down the road for now, it's only been Mine for a short time still."