Pegging Cuckold?

With that Jerry packed Dahlia's car and hopped behind the wheel. Pulling into his complex Dahlia says leave your spot 'H' open for my clients, tomorrows may be submissive bitches, but still my clients."

Once inside Dahlia instructs, "into the bedroom bitch, I want to make love, be sure to put one of your pillows under your caged clittie, I want to catch all that cum. Greg is going to breathe through that pillow as I plunder his cunt tomorrow morning."

Dahlia sleeps contentedly the sleep of the angels while Her bitch tosses and turns trying to figure out what had become of his life. On the one hand he was in submissive heaven, on the other he wondered where he'd left his manhood. He was finally able to sleep after accepting that manhood was over-rated.

8am Dahlia's alarm goes off; She smacks jerry on the ass. "bitch, I need coffee, and breakfast, Greg will be here soon to get his cunt fucked, I need protein and caffeine."

Even though he'd first suggested the idea jerry was still face with the reality that his goddess was going to be 'making love' to another man, in his bed soon.

Dahlia senses Her bitch's trepidation, "bitch, if Greg doesn't come on my cock which is unlikely as it will be my first time in his cunt; you will suck him off. Beg him to cum in your mouth. And when he cums down your throat you will thank him for it."

9:30 comes fast for jerry and when his doorbell rings he's brought out of his prepatory reverie. "I've got the door Goddess."

"Obviously bitch." Dahlia affirms.

Jerry opens the door to reveal a medium bult Asian man, Greg. "Hello, you must be Greg" Jerry greets his goddess's client.

"Hi" Greg says enviously, "you must be Jerry. You truly live the ultimate life you know?"

"More than you know my friend, " jerry says having found a kindred, submissive spirit.

"I look forward to hearing," Greg responds, "but for now, I need to service a goddess, your goddess. Will you please take me to her?"

"Of course, my friend," jerry says to comfort his fellow submissive, preparing him for the degradation and subjugation Greg will soon experience at the business end of Dahlia's cock.

Entering his bedroom where Dahlia had milked Greg's cock with Her mouth and pussy just days before, Dahlia was waiting. Effervescent in shimmering black patent leather which contrasted perfectly with her 8 inch pink cock. "Greg dear, give me a kiss." Dahlia beckons. "all I've had to satisfy my Womanly needs is this submissive's cunt," She says motioning derisively towards jerry. "I need a real kiss, from a man before I make him my bitch."

Jerry watches on, with tears on his eyes as his goddess shares a deep, sensual kiss with another submissive. Did Dahlia still kiss him like that? He wasn't sure, that looked so hot, so amazing.

"Now, bend over Greg," Dahlia instructs, "let me fuck you like the submissive little bitch you were born to be."

"Of course, Goddess Dahlia," greg says as his tight Asian ass accepts Dahlia's cock. But not much before jerry lubes her cock, Greg's cunt a little."

"Thank you cuck," Dahlia praises jerry with derision, "I guess you still have some uses, Greg does have a fresh cunt for me to enjoy. What else do you have to offer cuck?"

"Greg probably won't cum from your cock Goddess, not Your fault, It's just reality, I didn't cum the first time You made love to me either."

"You remind me of your failings cuck, and ascribe them to Greg here as well?"

"Yes Goddess," jerry admits, "they were my failings. But I've researched this a bit, it often takes a while for pegging bitches like myself to cum from anal alone."

"So, you are saying that Greg here may need more than my cock to cum this morning? Are you prepared to make sure that my Greg finishes?"

"Yes Goddess," Jerry admits, "Of course goddess."

"Good, then get to it cuck, make greg cum' and be sure to share it with him."

Jerry takes Greg's cock into his mouth as his Goddess continues to pummel the submissive's cunt. it doesn't take long before the Asian is spewing into Jerry's mouth. Reluctantly Jerry rises after Greg finishes to kiss Greg.

Greg resists, but Dahlia forces the issue, squeezing Greg's balls, 'accept my bitch's kiss slut"

Dahlia relishes the power of making 2, mostly heterosexual, men kiss; deeply, sharing a snowball. As the men break their kiss Dahlia grabs greg's face, holding his lips shut, "swallow bitch, swallow if you have any hope of being mine one day."

With that order Greg eagerly swallowed ever drop of his load, and like a baby bird opened his mouth yearning for more.

"Thank You Goddess," was all Greg could manage as he came down from his subspace high. "Thank You for the opportunity to be of service to you. and of course, your cock. and thank you alpha-cuck," Greg addresses Jerry, "for the opportunity to service Goddess with you."

"I wish I could say, 'no problem' my friend," jerry responded thoughtfully, "but it wasn't easy for me to watch my goddess's cock going in and out of your ass. That's how we make Love. But, I can't keep her cock to myself. That would be selfish. You should come back for more sessions; she has larger cocks once your hole is ready for them. Eventually you will cum just from her pegging."

"I will definitely be back," greg says excitedly, "any advice for getting the most out of these sessions?"

"Lock your junk up," jerry responds immediately, showing greg his own caged clittie. "Goddess caged me before She fucked me; so, it wasn't an option for me; but chastity helps set my mind right. This is a micro-chastity cage from Oxy-shop"

"it's so small, I'm not sure I'd fit" greg says with a worried tone.

Dahlia smiles overhearing Her cuck coach Greg. "They have other/larger cages sweetie." She tells greg. "But you'd fit into that micro-chastity cage I put My cuck in. Jerry was 7 inches before I caged him. less now, my girlfriend is down-sizing him into a flat cage later this week. Right before she fucks his cunt for the first time"

"I'm sold," Greg says, "stainless steel micro-chastity cage on Oxyshop you said?"

"Yes," jerry affirms helpfully, "use promo code 'Dahlia' to get 15% off." Jerry says proudly, having arranged the discount himself.

"I'll be your keyholder for $50 a month sweetie. you'll also get special rates on pegging sessions. Including spit-roasts with My Girlfriend. Caging sessions are $100 and include a free pegging."

The afternoon pegging session with Tim pretty much went the same. Tim was particularly excited to be locked up. "can I schedule the caging session now? can Your cuck be there as well? Can I please suck him while You peg me Goddess? It's always been a fantasy."

Dahlia laughs, "my bitch doesn't have much to suck anymore, even if he wasn't always in a cage. maybe My BFF Gabby can be there to fuck your face while I tap that ass of yours."

Tim sighs, "I was hoping to suck a real cock that could cum down my throat."

Dahlia laughs again, "again, My bitch doesn't have a real cock, just a clittie in a cage. I'll see if I can arrange a Bull for you; it'll cost extra you know."

Tim smiles, "of course Goddess, I expected as much."

Dahlia agrees, "sounds good sweetie, contact my bitch for scheduling once you know when your cage will arrive. If shipping is delayed you're still committed for that time, $100 plus the $50 fee for a Bull. Be a shame if you have to pay for 2 different caging sessions; as the cage is kind of necessary."

"Of course, Goddess," Tim admitted, "that makes sense and I do not want to waste Your time."

Jerry saw Tim to the door when Tim was ready to go; they shook hands, "I look forward to your caging session Tim."

Dahlia overhears Her bitch's farewell greeting. When Jerry returns She tells him, "I'm sure you will enjoy Tim's caging session; I'm going to ask Jeremy to be My Bull, and have Him breed you just before He and I spit-roast sweet tim. Extra seasoning for Jeremy's cock" She says with a wicked cackle. "Only question is, do I have Tim eat your chocolate cream-pie? Probably, I'd love to see My bitch cum from another bitch tongue-fucking his cunt."

7... Dahlia

The week went fast, it felt good for her to be topping bitches again. She pounded Cecil's hole in front of her pegging cuckold Wednesday evening before she destroyed her bitch's hole later that evening. It was hump-day after all. Thursday was going to be major, meeting his mom and all.

Jerry drove the 30 minutes to his mother Sharon's house where he'd grown up. Dahlia looked forward to seeing the room jerry grew up in. along the way jerry told Her he had 2 older sisters, Sue and Jane. No brothers. His mother Sharon was a widow his father having passed 10 years ago. His mother lived alone in the house he'd grown up in. Dahlia revealed some of Her personal history, She had no siblings, her parents had died in a car accident when she was 20. She was looking forward to meeting Sharon, it would be nice to have a mom again.

Dahlia teases jerry's clittie through his pants and cage while he drove, she cooed; "I know cuckie, you're excited to marry Me. How many groomsmen did he want? You know, Dogfart productions contacted me. Their studio president had done searches on the internet, "cuckold sessions" was found on My site. One of their most popular series. No, they weren't annoyed I was stealing their trademark; they were intrigued about our relationship and how I used cuckold sessions in my trade. We're collaborating on some ideas. I'll keep you posted. You tell me as I pull into my mother's driveway.

8.... Sharon

Jerry was bringing his latest Girlfriend by; great. She loved Her son, but he had the worst taste in women. The previous 2 had been a constant headache, a mental case in and out of the nut ward, and a narcissist. She hoped this Dahlia would be better, but she was suspect. She saw jerry pull up and like the gentleman she'd raised he stepped out and open the door for Dahlia. Fuck, she was Gorgeous! Sharon loved her son, but knew he was just average looking, assumed well below average like his father in other areas. Why would this gorgeous woman be with her less than average son? Having grown up in the house jerry opened the door and came right inside with his lady. "Hi Mom!" he said giving Sharon a hug and a kiss on the cheek. "I'd like you to meet Dahlia. Dahlia this is my mother Sharon." Sharon is unsure of things and offered her hand to Dahlia, who took it and pulled Sharon into a deep hug that caught the older woman off guard.

"Wonderful to finally meet you Sharon." Dahlia says warmly, "I've been trying to get jerry to bring me down to see you for weeks. He always made some lame excuse; but when he popped the question last week I put My foot down, I said I will not say 'yes' until I meet your mother"

Sharon is a bit taken aback by all the information and the mention of a proposal. "Thank you for that dear." she says with genuine warmth, "Jerry hasn't had the best judgement when it comes to women in the past. Thank you for reminding him that mom matters."

Dahlia pours on the charm, "damn right Sharon! My mom and dad died when I was 20. It's so nice to have a mom again!" Dahlia says, once again embracing Sharon in a deeper, even warmer embrace.

Sharon is thrown for a loop, "I don't know what to say Dahlia, You're not what I expected. Jerry is so average, less than in other areas knowing his father; and you are such a beauty!"

Dahlia smiles warmly, "just say you'll wait here and enjoy your coffee; I look forward to talking to you at length, but I'm dying to see the room Jerry grew up in."

Sharon sits down at the table and takes a sip of her coffee, "of course Dahlia, Jerry knows the way; I hope."

9... jerry

Jerry leads Dahlia upstairs and shows Her into the first room on the right. "that's my parents room across the hall from mine." he explains showing Her into his teenage room. Posters of scantily clad girls on the walls and model planes hanging from the ceiling.

"That's nice bitch" Dahlia says roughly as she throws him ass up in the middle of his old twin-bed. She pulls down his pants and pulls up her skirt to reveal her cock. Which she presses against her bitch's hole. "now try not to make your mother worry by making too much noise." She says as her cock slips into her cuck's hole. To his credit jerry keeps his mouth shut and hardly utters a sound.

The same cannot be said for his old, twin bed clearly not made for the animalistic sex it was supporting now; it strained and creaked loudly. Before long Dahlia forces a sissy-gasm out of her bitch, then not to be denied she pushes further to get the ass-gasm out of her whore that she sought.

"fuck Dahlia." jerry panted, "My mother? What will she think?"

"that you're a stud with an amazing woman." Dahlia says as she wipes Her cock off on my old bedding.

10... Sharon

The sounds of passionate sex from Her son's room were unmistakable. Sharon marveled that this Gorgeous Dahlia was so into jerry. But She heard the be upstairs creak with the young Lovers' exertions. Apparently he was more than his father was after-all. So much so that Dahlia had been in such a rush to take him upstairs. Sharon was surprised, to say the least, that her son offered so much; and more than ready to call Dahlia her daughter...

When they came downstairs Sharon greeted Dahlia with a warm hug, "I love You."

Jerry, feeling sidelined remarked, "I love you too Mom." As he rubbed his ass.

"Sit down with Me Dahlia, have a coffee. Do you want cream, sugar? Jerry would be happy to get it."

"Just cream" Dahlia says taking a seat across the table from Sharon. After jerry pours it for Her She indicates for him to kneel at Her feet as She talks with Mom. "Yes, jerry. Yes, I accept your proposal." Dahlia answers with a smile.

"Oh, this is SOOO exciting!" Sharon exclaims. "Welcome to the family Dahlia. Feel free to call me Mom. Now tell me, how did you two meet?"

Dahlia smiled and laughed a little, "Well mom, Your son hired me. See, I'm a personal escort. He hired me and we had a date."

"Oh," Sharon said non-chalantly knowing that the escort trade had been legal and growing in popularity for a decade now.

"Don't worry mom. I took care of his need to throw his little thing at women who he paid to take it right away."

So, he did have his father's curse Sharon observed. "how? But what was that I just heard with you two upstairs?"

Dahlia smiled Her most wicked smile, "Sharon, mom, I was attracted to Your son's submissive nature when we first met, so a few days after that initial date I asked him out. Before we went out I locked him in chastity; and then to conclude our date I pegged the fuck out of him for the first time. The sounds you heard before was me fucking the hell out of him on his teenage bed."

Sharon, rather than being shocked is intrigued. "Pegging? That's where a woman fucks a man in the ass isn't it?"

"Yes it is," Dahlia says intrigued by mom's interest, "speaking of which You might want to have jerry go strip his old bedding and wash it, "I had to wipe his ass off of my cock earlier; not to mentioned he ass-gasmed all over" Dahlia said showing mom Her cock proudly.

Sharon glares at Her son, "Jerry, you heard Your Fiancé, go strip and clean your old bedding, clean your filthy cunt and worthless seed off of it. So, My Dear," Sharon softens as she turns back to Dahlia, You're still working?"

"Oh yes mom, I am"; Dahlia says as She watches her bitch chastened by his surprisingly authoritative mother. "Yes, I know that makes jerry my cuckold. My chastity cuckold to be exact. But mom You won't believe how business has flourished with your son being my cuckold in sessions!"

"It's good to know he's good for something." Sharon says. It feels good for Her to finally be able to express Her true feelings about Her son who reminds her all too much of his 'less-than' father.

"I know what you mean mom," Dahlia says as She squeezes Sharon's hands, "but I think I've found his true calling as my cuck. His inputs for expanding my offerings to include My cuck have been considerable!"

"As I said," Sharon repeats, "It's good to know You've made use of him. too bad I was never able to do the same with his father."

"I am so sorry to hear about Your loss Mom, I know jerry looked up to his Dad." Dahlia comforts the older woman.

"Oh, not My loss Sweetie, jerry's father was as diminutive as jerry is; but less enlightened. I do wish things like 'pegging' had been a thing in the past. Or 'cuckolding' for that matter.

Dahlia decides to reassure her new Mom, "it's not too late mom, You're still vibrant and attractive. There are plenty of cucks in the sea. As far as pegging goes I'm planning workshops at our place after we move at the end of the year. Would you be interested?"

"Oh Sweetie, would I ever." Sharon exclaims rubbing Herself. "Sue and Jane would probably be interested as well; their husbands are less than if their complaints are to believed."

"I've never had sisters." Dahlia observed. "Should be fun. My pegging workshop I'd planned on using jerry as my lucky recipient for all attendees. It's typically best for either the Pegger or the pegee to be experienced. So, with a house full of novice Peggers, We need an experienced pegee; your son, My bitch would be perfect in that capacity. Would You be comfortable with that? would his sisters?"

"Dahlia," Sharon says gently, "you didn't have any brothers or sisters did You? His Sisters would love nothing better than to pound the fuck out of jerry's asshole! As for me, let me just say he is his father's son."

Just then Jerry returned from putting his old bedding in the wash.

"You ready to go Love?" Dahlia asks him with surprising warmth as she shares a mischievous glance with Sharon.

"Of course. Did you two have a good discussion mom?" jerry asks giving his mom a hug goodbye.

"Definitely Jerry. You chose a winner this time!" Sharon tells a surprised Jerry as his hard-to-relate to mother embraces his domme warmly.