I lifted a pair of rocks glasses to eye level. One was completely empty, but the other still had about a quarter of bourbon left in it, slowly diluting from the ice ball at the bottom. However, what really caught my attention were not the remnants of the liquid, but the deep red lipstick stains scattered in various places around the rim.

I closed my eyes and vividly recalled my wife applying that exact shade of lipstick. My mind transported me back to our bedroom, approximately three or so hours earlier. I was seated on the bed, watching her intently from behind, filled with the same affection and carnal desire that I had always harbored for her. She leaned close to the bathroom mirror and applied a thick layer of deep red lipstick to her perfectly shaped lips.

As my eyes traced her body downward, they traversed her bare shoulders and followed the deep inward curve along her side, accentuated by the black embroidered corset. My gaze continued on, lingering on her perfectly round ass cheeks suspended just above black, lace-topped stockings that flawlessly shaped her legs.

She must have caught me staring in the mirror because she turned around, the lipstick case still in her hand like a wand. She flashed her wide, alluring smile, revealing teeth that now stood out even more against her deep-painted lips, shining brilliantly white. She glanced down at herself and then back at me, wearing a confident and almost arrogant expression.

“Do I look pretty, dear?” she asked, but her presumptuous tone hinted that she already knew the answer.

“Stunning as always, my love,” I replied.

She smiled again, scrunching her nose and cheeks in a way that I had come to know as her mildly condescending “isn’t that cute” smile—a look I had witnessed many times, especially lately.

Turning back to the mirror, she began to sweep a soft-bristled brush across her face. “You look adorable too dear,” she concluded.

Upon hearing those words, I looked down at my own legs. They were also adorned with black opaque nylons, featuring a thicker top edge that wrapped around my upper thigh. These connected to a black and white skirt embellished with lace both on and underneath, giving it a lift off my legs. Adjusting myself on the bed, I could feel the thin shoulder straps attached to the skin-tight top wrapped around my torso subtly restricting my movement. After shifted my weight, the skirt moved just enough to reveal my imprisoned cock, securely enclosed within a metal chastity cage.

-x-

Hello there and thank you for allowing me to share our story. My name is Dan, and I’ve been married to my wife Kim for nearly thirty years. We were good friends during high school but lost touch during our college and young adult years. We crossed paths again at a local night spot, and to my benefit, she had recently become single.

Kim had a typical and stable upbringing, similar to most kids in the eighties. The focus was on achieving good grades, attending college, and avoiding trouble. She always carried herself with propriety and steered clear of certain cliques or negative influences. Throughout her dating years, she always had steady boyfriends because “that’s what you do.”

On the other hand, I also grew up in a stable home with similar values, but I must admit I enjoyed my late teenage years and early adulthood with the booze and one-night stands with multiple women.

Once we married, we settled into an average, middle-class family lifestyle. I held a corporate job while Kim worked as a teacher at our local elementary school. She dedicated her career to educating hundreds of children from our neighborhood and the surrounding town. Maintaining a professional and respected persona within the community was of great importance to Kim, especially since we lived in the same area where she taught. However, that also contributed to her repressive ideas on certain activities.

The only significantly challenging issue in our marriage revolved around Kim’s mother. As she grew older, she became increasingly difficult to deal with. Behind closed doors, she revealed herself to be a controlling woman and mother, exerting influence over much of Kim’s childhood and demanding that her children always cater to her wishes. Even after her children had left the nest, she tried to insert herself into their marriages and continue as a controlling presence in Kim’s personal life. This also contributed to Kim’s self-image issues.

On the other hand, Kim’s younger sister rebelled at an early age, engaging in simple acts of defiance such as smoking, drinking, and getting tattoos—typical reactions from individuals with controlling parents. Although she wasn’t nearly as attractive as Kim, I sometimes found myself fantasizing about her, imagining that she had a more explorative sense about her and probably engaged in the types of taboo acts that were off-limits to Kim.

Why am I sharing this with you? Well, it’s because our lives and marriage underwent significant changes a few months after Kim’s mother passed away. While it was a sad and unfortunate event, Kim no longer needed to maintain her defensive shield when dealing with her mother, and she was no longer subjected to constant scrutiny over every little thing she did.

Her personality changes started slowly.  She got a small tattoo on the top of her foot during a weekend trip with her girlfriends. Frankly, I was pleased to see it—a small sign that she was finally able to do what she wanted without fearing her parents’ disapproval.

But the more significant changes began innocently enough. Kim had always maintained long, dark brown hair that cascaded down her back, reaching just above her apple-bottom ass. Since childhood, she had refrained from cutting it, except for occasional trims of about half an inch to keep the ends neat.

One afternoon I was working in my home office, and a woman entered whom I almost didn’t recognize. She was clad in black stilettos, tight jeans that seemed as if they were sewn onto her, and a form-fitting black bodysuit that hugged her figure so snugly it could be mistaken for body paint. Her tits were pressed together and lifted, with a hint of lace peeking out from her bra. She looked as though she had just walked out of certain fantasies I had of my wife, but what caught me off guard was her appearance from the shoulders up.

Kim stood in the entryway, sporting a fresh pixie cut hairstyle that nearly knocked me out of my chair. It was expertly trimmed, allowing the layers of hair to gracefully frame her face. For the first time in our marriage, I could see her ears, adorned with jeweled earrings, and her alluring long neck, which was always concealed by her hair.

She looked up at me from beneath the finishing angle of her new cut, starting high on the left side of her face and tapering down just above her right eyebrow, with a vibrant streak of purple hair dye serving as a finishing touch. Forty-five years of continuous hair growth had vanished with a single snip of the scissors. I was stunned, and to be completely honest, my arousal mirrored my surprise as my cock instantly responded, swelling at the sight of this stunning woman standing before me.

“What do you think?” Kim asked sheepishly.

“What do I think?” I replied. “You look absolutely amazing!”

A bashful smile graced Kim’s lips as she asked, “Really?”

“One thousand percent,” I assured her, using my go-to phrase for when I was completely serious about something.

I rose from my chair and approached her, wrapping my arms around her waist. “What prompted you to make this change?” I inquired, trying my best not to sound judgmental and risk frightening her away.

“I don’t know,” she answered. “I... I just felt it was time for a change.”

“Well, I love it,” I responded. “Let’s celebrate. How about dinner at Carlo’s tonight?” I suggested, referring to our favorite romantic restaurant to demonstrate my excitement and full support for this new transformation of hers.

We had an amazing dinner, some drinks and ended the night with some fantastic lovemaking. Mostly missionary of course, but I was so happy to be able to kiss and suck on her gorgeous neck and shoulders without inhaling a mouthful of hair for a change. 

Our marriage carried on relatively unchanged, but I began to notice gradual shifts in Kim’s personality over the following months. The bottles of our favorite wine were slowly being replaced with stronger spirits. She started disliking her old clothing, leaving piles of it by the door for me to donate to Goodwill, and replacing it with sexier shoes and more body-revealing outfits.

The transition had begun.

-x-

I spun the rocks glass slowly in my hand, carefully examining each individual lipstick stain. I could almost hear Kim’s laughter and feel her seductive presence as she left her mark on the glass. I then turned my attention to the other glass. I recalled his strong hands, nearly enveloping the vessel, and his deep, throaty voice as he looked my wife up and down.

As I studied the pair of glasses, my imagination took hold, transporting me to a deep recess of my mind. Thoughts like “How did I end up here?” and “What is happening?” raced through the confines of this mental space I had trapped myself in. However, I could feel myself quickly pulled out of that room, and in a sudden jolt that caused my body to tremble, I was abruptly brought back to reality.

I looked up drowsily at the staircase leading to the second floor, where our marital bedroom was located. I could hear the deep moans and the sounds of sex and intense pleasure coming from there. I heard bodies and raw skin slapping against each other in rhythm. I heard furniture creaking and glassware rattling. And above it all, I could hear my wife’s distinctive voice screaming things that I never heard her say when we used to make love.

“Ohhhhh fuck! Fuck me harder…..yes…yes….fuuuuck!” she shouted at what seemed like the top of her lungs.

Her cries were met with deep grunting noises and the occasional sound of a hand slapping skin repeatedly.

I shook my head, bringing myself back to reality. With a humbled sigh, I turned towards the kitchen to clean these glasses and the remaining dishes from their dinner. With each step I took in my black nylon-covered legs and frilly skirt toward the back room, their cries of ecstasy grew fainter. I could still hear them, but it was now simply background noise as I resumed my chores.

I’m not going to lie, as I heard her screams of pleasure, my cock leaked precum from inside of its metal prison. He must be pressing buttons deeper inside her than I ever could, to make her react like that. But I couldn’t focus too much on their activities because I had chores of my own, and I did not dare risk angering Kim if she found everything not completed to her standards.

I washed the plates that they ate off of from the dinner that I made for them. The silverware that my wife pressed against her ruby red lips as she flirted with her lover. Their rocks glasses once filled with the bourbon I prepared for them, meant to loosen up their inhibitions. These were the last things to touch their lips before their bodies did—kissing and licking each other’s bare skin before moving their private party upstairs. 

Soon, I heard my phone chime from behind me. It was Kim’s personalized ringtone so I knew I had to answer it. I opened the phone and saw a text addressed to “Diane.” That was the name she gave me whenever I am dressed as her maid or in other feminine attire. It was close enough to Dan, but not close enough to ever be confused for a masculine one.

“Diane, bring up some champagne to cool us down. Two glasses.” the message read.

I replied with a quick “Yes Miss” and reached for the bottle in our beverage refrigerator.

I poured both drinks and hurried up the stairs. My metal chastity cage swung uncomfortably with each rapid step. I entered the room holding a glass in each hand. He was on the far side of the bed, sitting up with his back against the headboard and completely naked. Kim was lying closest to me, on her side, with her head on his chest and lovingly stroking his huge flaccid cock. The corset she had originally been wearing lay on the floor, but she still had on her stockings and heels.

She looked up at me and swung her knee upward, opening herself up so I could see the small, soft patch of dark pubic hair she kept. It was drenched in sweat and bodily fluids while a thick white puddle of cum oozed from her freshly fucked pussy. I handed both of them the glasses and moved towards her legs, expecting the command to clean her.

Kim stopped me with her hand and said, “No dear, not now. I expect to be fucked again after this drink and I want to feel every ounce of his cum inside me.”

She wiped a strand of cum off of her inner thigh and lifted her hand toward my mouth, pressing her fingers between my lips. I could taste the salty freshness of his seed. Holding them there for just long enough for me to taste it all, before extracting them from my lips. Turning her hand over, she took hold of my chin for my complete attention.

“Now be a good maid and go prepare dessert for us, while we prepare dessert for you.” she sneered, punctuating the line with a snide “OK?”

I nodded in response. She released my chin and turned her hand over to wave me off and shoo me out of the room, snuggling her head against his muscular chest before the gesture was even completed. I retreated to the kitchen and placed the dessert I had prepared into the oven to warm it. Shortly after that, I could hear them starting up once again and the unmistakable sounds of carnal sex resumed.

After a while, I heard the sound of heels clicking as they descended the stairs. I hurried to finish setting the table. Two place settings are all that would I would be allowed to set because my reward for being such a good maid would not be served to me off of any plate.

She entered the dining area first, with him following closely behind and being led by the hand. They were both still naked except for her stockings and heels, as she was before. They settled into their seats, and I brought out their dessert: Warm apple dumplings that I made from scratch served with a side of vanilla ice cream that was melting just enough to drip down around the hard crust beneath it.

“Mmmmmmm, thank you dear,” Kim complimented. I stepped back and waited for my next order, standing there in my black and white maid uniform, stockings, Mary Jane-style heels, and my ever-present chastity cage. Kim took her spoon and scooped up some of the melted ice cream. She brought it up to her face and let it dribble off, landing on her outstretched tongue. She swirled her tongue around and then sucked it into her mouth with an exaggerated slurping sound. They both laughed deeply before she redirected her focus back at me.

“This is delicious dear,” she said, “It reminds me of exactly what you’ll be having for dessert.” Her comment was interrupted by his deep masculine laughter.

They looked at each other and shared a final giggle. I didn’t have to wait for another command. I knew exactly what she meant.

“Yes Miss” I replied and sunk down under the table and positioned myself between her slender legs.

I was inches away from her glowing pussy. Ripe and red from being abused, it glistened with wetness even under the table where there was little light. I could see the bubbles of fresh cum escaping and starting to trickle down the edges of her pussy lips.

Kim cleared her throat in an authoritative way. It clearly was directed at me as a sign of her impatience.

Afraid of angering her further, I pressed my mouth onto her soaked pussy. It was so wet and fragrant. My tongue did most of the work initially, acting as a similar type of spoon that they were using to enjoy their dessert above me. Lick after lick, I scooped up what felt like gallons of cum. Tracing both of her labia lips before licking straight up the middle. I slurped inward at the end of each upward motion, consuming the thick seed he injected into my wife. I listened as their conversation was interrupted by the occasional sigh or soft moan from my wife, which motivated me to keep going.

My face was fully coated in a warm, sticky cocktail of their orgasmic juices. I moved to her inner thigh and cleaned up any stray traces that may have landed there, even the ones that had soaked into her stockings. Inspecting the area once more, I could tell that she had been sufficiently cleaned.

In my desire to continually please my beautiful wife, I returned my mouth to her pussy and started flicking my tongue over her protruding clit. I heard her gasp in pleasure from above and then release a soft, almost instinctive giggle. However, my attempt to pleasure her was canceled when she kicked me away with her leg. Apparently, she was not interested in receiving any additional pleasure from me beyond the scope of my cuckold duties.

I stayed under the table on my knees as they continued to eat and converse above me. She crossed her legs in a definitive sign that her pussy was officially off-limits to me. As hurt as I was by the denial, she teased me by dangling her stiletto off of her toes, fueling my obsession and keeping my lust growing, both in my heart and inside my cage.

Soon the silverware stopped clinking, and their conversation turned to a more sexual nature. I assumed that they were close to finishing. Kim uncrossed her legs and gave me a soft kick against my bottom to make sure I was paying attention.

“Dear?” Kim called out.

“Yes, Miss?” I replied from under the table.

She continued, “We are finished and want to begin fucking again. However, my date is not yet fully aroused, and my mouth is just so tired after that delicious dessert.”

My shoulders sank in anticipation of what command would come next. I could see it coming from the moment they both sat down naked.

“Be a good maid and take care of that problem for him,” she requested, just as I had assumed.

I didn’t do a very good job of masking my reply, “Yes Miss” I said in a tone that sounded defeated.

“Aw, does Diane not want to do her job?” Kim questioned sternly. “You know how much I want Diane to enjoy her position here, correct dear?”

I spoke up clearer “Yes Miss, of course, I enjoy….”

Kim interrupted, “Don’t you mean Diane…”   

“Yes, my apologies. Diane enjoys her position here very much Miss.” I corrected.

“Good, now get to it Diane” She ordered in a tone that signaled that those were the last words to be spoken on the topic.

I slid across and under the table. He spread his legs, exposing his massive cock. It hung down between his legs like a thick tree branch. I could now understand why Kim was screaming the primal sounds that she had been making earlier. I held the monster in my hand and slipped between his legs. I could hear them giggling softly above me. Not interested in any foreplay, I opened my mouth wide and just stretched my lips over his mushroomed head. My eyes squinted and watered as soon as my lips touched his shaft.  My mouth felt completely full with only the tip inside of it.

I’ll admit, I’m not the greatest cocksucker just yet. This is an act that Kim has only recently introduced into our journey toward me becoming her full-time cuckold husband. I’m sure this is just one more lesson on my path toward becoming a better cuck for her and her lovers.

I pushed it as far back into my mouth as I could without gagging. I began to bob my head up and down attempting to only use my lips and tongue which is not an easy thing to do when your mouth is stretched so wide. My tongue licked the underside of his cock, hoping that would provide some level of satisfaction while my hand moved up and down the rest of his shaft.

My eyes widened as I felt him growing inside my mouth. “Oh, no,” I thought, “how can my mouth fit anymore?” I pulled away from him and watched as his thick slab of flesh seemed to double in size and stiffened to the firmness of a steel beam. My hand continued to jerk him softly as my tongue moved around his bulbous head.

With that, I felt a bright light flash over me. Kim had thrown the tablecloth back across the table and now she was staring at me through the thick glass pane as I knelt there and sucked another man’s cock for her. The expression on her face was one of pure enjoyment and mischievous pleasure.

From the corner of my vision, I saw Kim’s legs strut from her chair over to his. She took his hand and gestured for him to stand up from his seat. Doing so, he pulled away from me and stood just outside the edge of the table. Not receiving any commands to stop, I crawled over and knelt directly in front of him, preparing to suck again.

But Kim got between us and began to passionately kiss and explore his naked body with her hand. Unsure if my job was complete or not, I knelt there obediently, waiting for the next directive from Kim. She lifted her leg and wrapped it around his hip allowing his cock to slide out under her raised leg. Her hand moved from his body to my head and with a gentle push, guided my head under her leg and back onto his stiff cock.

I sucked it as deep as I could with her hand pushing and pulling on me in suggestive support. Her leg relaxed and fell across my shoulder and behind my head, preventing me from moving off of him until she felt my job was completed to her satisfaction. I felt her thigh moving in harmony with her hand, adding more pressure on the back of my head and forcing more and more of his thick rod down my throat. Tears raced down my cheeks and I uncontrollably produced raw gagging noises which were far from pleasurable, except perhaps to them.

Finally, Kim believed he had regained adequate hardness and she forced me off of him with her leg. I hit the floor coughing and dripping saliva from my mouth. I don’t know if he came at all in my mouth or not because it was all such a euphoric blur.

I managed to regain my composure and got back on my knees only to see the two of them walking out of the dining area, hand in hand and headed for the stairs. I knelt there for a few more minutes, panting and feeling the pain in my jaw from the massive log I was forced to service. I eventually returned to my feet, straightened my outfit, and started clearing the dishes once again. From upstairs I heard waves of noises roaring and subsiding at alternating times throughout the remainder of the evening.

It was getting late and eventually, the noises subsided, signaling that my services were most likely not going to be needed for the rest of the evening. Knowing that our marital bedroom was fully occupied, I retired to the guest bedroom on the main floor.

I hung up my maid outfit and slipped out of my heels and stockings. I went to bed wearing only my chastity cage, as it is a standing order from Kim for whenever I am sleeping alone. She wants me to always be reminded of who truly owns the cock that I walk around with.

I set my alarm early enough so I can prepare breakfast for them if they desire it and I fell asleep with the wet trickle of more precum sliding down my leg.

To be continued.