Let me just say first that I am happily married and I am a proud cuckold — and those things are not at all mutually exclusive. My wife, Betty, is truly a stunner. She’s an insatiable brunette BBW, who could take on legions of men in one evening if she had her way. Knowing her sexuality is part of who she is, it’s never bothered me that she needs “more than average” to be satisfied. As it happens, I’m “less than average” below the belt, and I maybe have half of her libido. However, we make it work and remain as madly in love as ever.
I’ve always been happy to let her take on other lovers — men or women, whatever she needs to feel good. I’m not emasculated or threatened by my wife’s cravings. Dare I say, it’s always a good time when her pleasure ultimately leads to some wicked fun and sexy humiliation for me. Betty’s always been dominant and bossy, and I’m naturally submissive, so our needs mesh well.
We frequently enjoy male sissy roleplay and male chastity games to spice things up. For instance, one time she made me clean the house wearing her pink satin thong panties and one of her sheer chemises, while she fucked another man on the sofa in plain view. I had to keep vacuuming, dusting and tidying until Betty was spent, which took almost two hours!
I’ll tell you what: You’ll never forget the sight of a big-dicked guy splitting your wife’s fat cunt in half while you’re trying to polish the coffee table.
As the lovers moaned in pleasure, sometimes they’d glance at me with wry smirks, clearly mocking my predicament. The flushing of my face and the pain of my constrained cock had me floating on another plane of being. But as her sissy maid, I also had to mop up the leather couch after they were finished rutting in front of me.
After Betty’s conquest left, we relaxed in our spotless home alone, and she partially yanked down my thong and took my tiny dick out of its steel chastity cage.
“Let me see him now,” she ordered.
Free of constraint, my cock sprung to attention — as much as it could naturally.
“He’s happy to see you,” I told her.
Betty spat in her hand and took my knob between her fingers as she clucked, “It’s going to take me all night to milk this pitiful caterpillar into a respectable length.”
Her mocking my dick is not at all a real insult. It’s all part of our fun — and seeing her roll her eyes and shake her head while tugging and tugging on my small shaft always makes the day’s stress and frustrations worthwhile.
As she worked me that night, I held my breath and tried to stay focused so I’d last as long as possible. It’s such a turn-on feeling her “use” me like a stud for milking. Five minutes in, Betty stopped and sighed in fake frustration over her inability to coax any additional length out of my puny penis.
“I guess we need to take more drastic measure,” she said, shaking her head forlornly. “I’m so disappointed. You should be ashamed!”
She punctuated her words with a swat to my behind.
I knew what was coming next. To compensate for my lack of endowment, my wife and I own many different dildos and toys, but only recently has Betty taken a fancy to pegging me. At first, I wasn’t sure about trying it, but the act has opened up a whole new avenue of pleasure for us.
Betty got up and retrieved one of my favorite prostate toys.
“I’m not going to fuck you tonight,” she stated matter-of-factly. “But we’ll need to extract some of your spunk or you’ll get backed up, and that isn’t good for you. Now, take off your lingerie and get into position.”
I nodded and stripped out of the chemise and thong. Even though I’d cleaned up her and her man’s puddles of love, the couch was still warm from all their action. I could also still detect the scent of cuckold sex as I assumed a prone position on the sofa.
The toy Betty shoved into my ass had a narrow shaft that vibrated — and if you’re a guy and you’ve never experienced a prostate orgasm this way, well, let’s just say it’s the closest you can get to walking on the moon without being an astronaut.
Betty turned the dial on low, keeping the vibrations faint as she resumed pulling on my small shaft.
“Feel good?” she asked.
I groaned and nodded in response.
“You make such a sexy maid. I loved watching you wiggle your little ass as you vacuumed the floor while I came.” Then, without warning, she cranked the vibration to maximum speed.
That, and a sudden flashback to our illicit afternoon of play, quickly pushed me over the edge. I blew my load, and it landed all over the discarded chemise. To make up for this clear transgression, my wife made me do the laundry while she soaked in the tub.
Anyway, with such an unconventional sex life, it’s always a challenge to find ways to up the ante on special occasions. However, this past autumn — for our fifth anniversary — I think I did us proud.
Usually our cuck sessions are with other men, but on a lark, I connected with a local domme named Melinda, who loves strap-on sex — and she agreed to help me surprise my wife!
As if watching two beautiful women make love wasn’t already hot, I was to be cucked by one for our special night!
Betty and I rented a hotel room downtown for the occasion — and just as my wife and I were toasting with our champagne flutes, there was a knock on the door.
“Are we having company?” she asked, already assuming the answer and looking pretty excited about it.
“Uh-huh,” I said before kissing her. “I think you’ll be pleased.”
I got up and opened the door — and, wow, Melinda did not disappoint!
She was around our age with beautiful dark skin and flowing relaxed hair that fell just past her shoulders. With her spiked heels on, she was taller than my wife. She was also more narrow, but still deliciously thick in all the right places. She strutted inside and unbuttoned her coat to reveal a red latex mini dress.
“I heard we’re having a party tonight,” Melinda purred.
My wife beamed and looked from her to me as she said, “Oh, hell yeah!”
Melinda laughed and told her, “You have a very wonderful husband, lady.”
“I definitely do,” Betty replied. Then she gave me a kiss and an order: “Go put on your cock cage.”
She didn’t have to tell me twice! While the ladies chatted and got acquainted, I went into the bathroom and stripped down. The cock cage for that evening was an extra-special device, in that it had a built-in butt plug to add to my torment. As it happened, I was already dealing with a semi-erection, so the orgasm denial that night would be on another level.
“Hurry up!” Melinda called. “I don’t think I can make her wait any longer.”
I stepped out of the bathroom to find the girls already on the bed. Melinda had Betty’s armed pinned back and her big floppy tits exposed.
I exhaled sharply and felt dizzy.
“Focus, honey,” Betty called out, sensing my bewilderment. “We’re counting on you to record us.”
I grinned and picked up the video camera one of them had placed on the dresser.
“I’m ready. Just…pretend I’m not even here,” I told them.
“Well, that’s no fun,” Melinda said in a fake pouty voice. “You’re here, and you’re in a sad little cock cage because I have to please your wife for you. I heard you’re just not big enough for her.”
“Mmm, no I’m not.” I hit “record.” Try as I might, there was no stopping the rush of blood to my small dick as I filmed Melinda and Betty kissing and teasing each other’s breasts. I made it a point to zoom in on Betty’s face, and seeing her obvious pleasure as Melinda went down on her almost made me lose it. I looked down and took some deep breaths to steady myself and then returned my attention to the lusty lovelies before me.
Once Melinda had Betty’s pussy nice and wet and aroused, she slipped on her leather harness and attached a giant black cock.
“Make sure you get a good shot of this, Will,” Betty called over to me.
“It’s bigger than any human man! Wow!” I exclaimed.
Melinda interjected, “Yeah, well, we definitely know he won’t measure up.”
“No, he could never compare to this,” Betty marveled. “Mmm, don’t make me wait anymore.”
I bit my lip and zoomed in on Betty’s soaking gash as Melinda teased her opening with the head of the massive dong.
“Ready for this?” Melinda asked.
Betty nodded and then gasped loudly as her pussy was stretched by the dildo’s girth.
My poor prick strained against the metal cage as I watched my wife’s arousal skyrocket.
Melinda started out in missionary position, but Betty wanted the chance to experience the “black stallion” in every way possible. They switched to doggy-style for a bit, and then positioned Betty on top, riding the toy like it was a bucking bronco. All the while, I reveled in the sight of her voluptuous body accepting that silicone monster.
Betty squeezed her tits together and glanced over at me to say, “Like what you see, Will?”
“Oh, yes. You’re a goddess, my angel,” I replied.
“Hey, what about me? Melinda interjected.
“Oh, God. You’re beautiful, too,” I sputtered.
Melinda spat out, “You’re just jealous of my cock!”
My wife smirked and whispered something to Melinda. Then she dismounted the dick and motioned me over to the bed.
“Join us — you’ve earned a little something,” Betty said.
At that point, I left the camera on the chair and went over to the bed. My wife freed my poor member from the cage and gently removed the butt plug.
“He’s been taking this like a champion,” Betty told Melinda as she patted me on the bum. “Wait until you see what he can do.”
Melinda switched out her strap-on attachment and lubed up a swirling blue shaft that was more realistic in size — but it was definitely bigger than any dick I’ve had in my back hole.
Over I went, and Melinda eased the toy into my ass as I orally pleasured my wife. Once Melinda began actively fucking me — and smashing my face into Betty’s wetness with every inward stroke — it was all I could do to try to bring Betty over the edge before me. But before I could make my wife climax, I peaked, collapsing between her thighs and feeling my warm jizz pooling on the comforter below me.
The ladies laughed and high-fived each other. But really, sandwiched between those two women, no man — or sissy — could stand a chance!
“Happy anniversary,” Betty said, giving me a kiss on the forehead. “Thank you for the perfect evening.”
Spent, humiliated — and absolutely thrilled — I drifted off into a blissful post-coital sleep while my wife and Melinda carried on without me.