HER PROPOSAL

I’d been pestering my wife for ages about letting me fuck her in the ass. She was an anal virgin and understandably cautious, no matter how many times I tried to persuade her. Then, one night out of nowhere, she looked over at me and said, “If you’re so obsessed with anal, maybe you should try it first.”

I just stared at her, wondering if she was joking.

She wasn’t. She told me flat-out that if we bought a strap-on and she saw me genuinely enjoying it—really enjoying it—then she might consider giving up her anal virginity.

After that conversation, my mind wouldn’t leave it alone. She meant it. And once she started casually browsing strap-ons and pegging videos—drifting into cuckold-sissy clips—the whole thing twisted into something even hotter. The more I thought about it, the more it turned me on.

SHOPPING — TOYS

The next weekend, we went shopping.

Before we left, Sue paused at the bedroom dresser, a small, knowing smile touching her lips. From one of the drawers, she took out a pair of lace panties, folded and delicate. The kind that made my pulse instantly pick up.

“Put these on,” she said, holding them out casually. “They’ll help you remember what today’s really about.”

Her tone was light but decisive, leaving no room to argue. I hesitated for a second, long enough for her to tilt her head and raise an eyebrow, then took them from her hand. As I slipped them on, the reminder against my skin felt impossible to ignore. Sue watched, quiet and satisfied.

“Good,” she said at last, smoothing her hair in the mirror. “Now you’re in the right frame of mind for our little outing.”

I drove the thirty minutes into town while Sue sat beside me, one leg crossed over the other, calm and composed in a way that made my hands feel clumsy on the wheel. The hum of the tyres filled the silence.

After a few minutes, she spoke, light but intentional. “By the way,” she said, glancing at me, “I slipped a little something into your morning vitamins.” I shot her a quick look, half curious, half nervous. “Nothing dramatic,” she continued. “Just something to help you stay… attentive.”

The word hung between us, deceptively casual. I knew what she meant. My occasional Tadalafil. But how much?

The air in the car suddenly felt warmer. Every sound seemed sharpened: the engine, my breath, the soft rustle of her sleeve. At the next red light, she turned fully toward me, studying my face. “Comfortable?” I nodded, though the word felt thin. “Good.” Her smile was small, deliberate. “Then stay that way. Present. Aware.”

Her hand settled lightly on my crotch. Just a touch, enough to send a jolt through me. No commentary, no need. The gesture alone made the dynamic unmistakable.

When the light changed, she faced forward. “Remember,” she said softly, “it’s only shopping. Try to behave like it.” The irony left the silence between us electric.

Our first stop was the sex shop. My heart was pounding as we walked in. Walls lined with toys, restraints, lubes, and straps. Overwhelming. She, meanwhile, was in her element: excited, giggly, and confident. I was already half-hard from the setting alone, which was humiliating enough.

We moved to the strap-on section, staring at the rows of harnesses and dildos: veined, bendable, vibrating, and some monstrously thick.

“Which one do you want to try in your pretty little bum first?” she asked, loud enough that I instinctively glanced around.

A young sales assistant, a curvy brunette in a tight black dress, name tag reading Chloe, was nearby. She caught my eye and smiled. A knowing smile.

“I’d recommend this one if he’s just starting out,” Chloe said, stepping in smoothly. She held up a kit with three dildos: a 4½-inch beginner, a more average 6½-inch, and then the full 8-inch monster. Each thicker and each more intimidating. “Start small. Work your way up.”

Her eyes flicked down to my crotch.

I was tenting my lightweight summer linen trousers. She definitely noticed.

Her gaze lingered a beat too long before she looked back at Sue.

My wife laughed. “Oh, he’s already working his way up, can’t you tell?” she said. “He’s wearing his favourite lace panties today to get him in the mood. There’s not much restraining him.”

Heat flooded my face. Chloe let out a soft, professional laugh that didn’t hide her amusement. “You’ll need plenty of lube,” she said, nodding towards the shelf.

Sue loaded bottles of lube, anal relax spray, and douche kits into our basket. I tried to look anywhere but at people.

Then Sue added lightly, “Oh, and what about little accidents? Too much excitement, too early?”

Chloe smiled knowingly. “Happens more often than you’d think. A little structure can help. Keeps things under control.”

She led us to a glass case of chastity devices. I played the curious beginner, despite secretly owning several types already, while Chloe talked us through the designs with professional ease.

Sue leaned closer, fascinated. “There’s quite a range.”

“It depends on how strict you want to be,” Chloe said. “Some are about reassurance. Others about… discipline.”

Sue smiled, slow and knowing. Chloe selected a firm but manageable model. “A good starting point.”

Sue examined it, then nodded towards a smaller, harsher one. “And that?”

“That one’s usually for very disciplined couples,” Chloe said. Her eyes dipped briefly toward me. “It limits enthusiasm and can be… challenging for beginners who aren’t on the smaller side.”

Sue laughed softly. “Then perhaps that’s for later.” The chosen cage went into the basket with a metallic clink that seemed absurdly loud.

Chloe then added, conversational and amused, “We do have private booths for fittings. Or a more open area if you prefer something… adventurous.”

Sue’s eyes glimmered. “Not this time. Maybe when he’s more seasoned.” She paused. “Although… do you ever guide couples through it?”

“When asked,” Chloe replied smoothly. “A little structure helps. Makes the first time easier.”

Sue nodded. “Reassuring.”

At the counter, Chloe packed everything: lube, sprays, cleaning kit, the strap-on, and the cage into a bag with the shop’s name in looping gold script. Nothing hidden. Nothing discreet. “That’ll do nicely,” Sue said.

“It’s quite the starter collection,” Chloe replied, handing over two slim booklets. “They cover fitting, communication, boundaries, and bonding. This kind of exploration can lead to surprising places. People often discover parts of themselves, or each other, they didn’t expect.”

Sue’s interest sharpened. “Good to know.”

Chloe smiled. “Take your time. And if you ever want guidance, we’re here.”

“We’ll find our rhythm soon enough,” Sue said softly.

Chloe’s smile deepened. “I don’t doubt it.” She slid the bag to me, letting the symbolism speak for itself.

As we turned to leave, Sue added brightly, “Let’s get matching lingerie next.”

Chloe laughed. “Then you might want those private booths. They’re popular when couples start coordinating.”

Sue paused, amused. “Maybe next time. We’ll take our time at home first. But who knows, perhaps soon we’ll be ready for something… guided.”

“Whenever that time comes,” Chloe said with quiet certainty, “you’ll be well looked after.”

Sue’s final smile promised everything.

As we stepped toward the door, I could feel Chloe’s gaze following: polite, amused, and utterly sure we’d be back.

SHOPPING — LINGERIE

We walked into a nearby boutique with soft lighting, satin draped everywhere, and mannequins dressed in sheer lace that made my stomach tighten. I was already flushed with embarrassment, but she wasn’t done with me. She headed straight to an assistant, a tall blonde in her thirties, and said, with perfect calm, “We’re looking for lingerie for both of us.”

The woman blinked once, then smiled warmly. “What kind of look are we going for?"

“Something matching,” Sue said. “Sexy, lacy. Black for me, and something brighter for him. Panties and stockings, of course.”

The assistant gave me a playful once-over. “Adorable. I think I’ve got just the thing.”

Before leaving, the assistant paused beside Sue with a friendly, practised smile. “Just quickly, your sizes?” she asked. “Panties and bra. I want to make sure the sets we bring actually fit you both.”

Sue gave her panty size easily enough, but the moment the assistant asked for her bra size, her eyes flicked down to Sue’s chest, lingering, just a touch longer than professional necessity.

Sue noticed. I noticed. “Thirty-six double D,” she said, lifting her chin with a little amused pride.

The assistant nodded, but her expression said she’d already guessed. Of course, she had “Perfect. Thank you. I’ll bring coordinated pieces for both of you.” She gave me a cursory once-over as well.

The two assistants returned together, arms full of deep black lace for Sue, and vivid crimson for me. Stockings, suspenders, delicate panties… and bras.

Sue’s eyes widened the moment she spotted the pair of them.

“Oh, a bra for him too?” she said, surprise melting instantly into delighted amusement.

The lead assistant smiled as she handed Sue the full, elegant black bra, then held out the smaller, softer padded cup toward me. “Well,” she said gently, glancing again at Sue’s full breasts, “You obviously needed one, and we wouldn’t be able to call the sets truly matching unless he had one as well.”

Her tone made it sound like the most natural thing in the world.

Sue laughed under her breath, thrilled, and picked up the black lace bra for herself, holding it against her chest admiringly before draping it over her arm. Then she turned to me, lifting the vivid crimson pieces from the assistant’s hands and passing the bra to me deliberately.

“Take this,” she said, her tone light, but threaded with unmistakable authority. I swallowed and accepted it. The flimsy bra seemed to radiate heat against my palms.

Sue raised her eyebrows and nodded. “Hold it up so I can see.”

I lifted the small crimson bra, trying to imagine how the hell it would sit on my chest. Sue watched me for a beat, her smile deepening. “Oh yes,” she said softly. “We’re definitely doing this.”

The assistants exchanged quiet, delighted smiles. The contrast between us was absurd. Her cups were full and natural, mine barely shaping the air, but she looked delighted. “Oh, that suits him,” she said, glancing at the assistants with a conspiratorial grin. “Good choice, the colour perfectly matches his complexion.”

They giggled together.

I was so red I thought I might faint. My cock was visibly fully erect now, straining against my trousers, and I could feel myself leaking in front of both women.

One assistant nodded thoughtfully.

“We can include soft inserts if you like,” she said, her tone warm and professional but carrying that quiet, knowing amusement women get when they’re already imagining the final look. “They really help with the fit and give a smoother, more realistic line. And… they make the overall silhouette look much more natural once everything is on. Especially for someone of their shape.”

The way she said their shape, as if I no longer belonged to the category of men at all, sent heat rushing up my neck. It felt clinical, considerate… and devastatingly humiliating.

Sue turned to me, eyes glinting. “Hear that? They think of everything.”

The second assistant left briefly and returned with a handful of inserts in various shapes. Sue chose a small but perkily rounded pair and tucked them into the cups while I still held the bra against myself.

“Oh yes,” she said, admiring the effect. “That looks about right, don’t you think?” I nodded, unable to speak. Sue and the assistants could barely keep straight faces.

At that moment, the boutique door opened. A few other customers came in, glancing around casually. One woman paused mid‑step as her eyes swept across the room and then landed on me. Me, standing there holding the bra up, inserts tucked into the cups, my cock straining visibly against my trousers. Her lips twitched into a knowing little smirk before she moved on. Another couple wandered nearby, pretending to browse, but their eyes flicked back to me more than once.

Sue ignored them completely, her attention fixed on me with a glow of ownership that made my stomach flip. The assistants stayed professional, but I caught the subtle, amused glances they exchanged when they realised how hard I was.

“Oh yes,” Sue murmured, admiring the effect of the inserts. “That looks about right, don’t you think?”

I couldn’t meet anyone’s eyes. Their expressions weren’t mocking, just interested, kind, and quietly amused. What had once been a private indulgence now hung openly between us, transformed by Sue’s confidence into something no longer secret, just real, and dizzyingly intimate. I could only nod. Sue and both assistants were fighting smiles.

One assistant’s gaze dipped lower, to my crotch, where my erection pressed insistently against the fabric. She lifted the tag on the panties and said gently,

“We may have underestimated his size. These might come up a little small. I can bring the next size if you’d like. He could try them on. Although with delicate fabrics like this, it can be tricky if they become… marked.”

Sue paused for only a heartbeat before smiling.

“No, these will be fine. And I think we’d end up having to buy them if he tried them on,” she said, glancing pointedly at the tent in my trousers. “They’re meant to fit close, and they’re only one size smaller than what he’s wearing now. And we have something to ensure a tighter fit…”

Her eyes dropped to the open shopping bag resting at our feet. Both assistants followed her gaze. One stiffened in surprise. The other’s mouth curved into a slow, delighted smirk.

The steel cock cage lay in plain sight, resting brazenly atop the strap‑on dildo.

“Ah,” the smirking assistant said softly. “Then yes, these are definitely the right size.”

The other assistant nodded, composure returning. “Absolutely. Once he’s inside that, the fit will be perfect.”

Meanwhile, the customers had drifted closer, pretending to browse or ask questions, but their real focus was obvious. Their eyes darted toward the bag, then to me, then to Sue. A few exchanged half‑suppressed laughs and smirks. They trailed behind us to the till under the flimsiest pretense of asking about returns, only to keep sneaking glances at the toys and at me.

My humiliation burned hot and sweet. Sue drank it in. She leaned toward my ear, her breath warm, voice dripping with wicked delight, “Oh my god, you’re so turned on. Everyone can see how much you want this.”

My hands shook as we paid. The assistants kept polite smiles, but they weren’t fooling anyone. And the woman next to us in line wasn’t fooling anyone either. Pretending not to notice the gaping sex‑shop bag with the cage, the dildo… and the breast fillets the assistant had casually laid beside them, even though we didn’t choose them.

She noticed. They all did. I couldn’t meet a single pair of eyes. Sue, by contrast, practically glowed with satisfaction.

As we stepped outside, she leaned in again, her voice low and molten:

“You’re going to be such a pretty little anal toy tonight.”

DRIVE HOME

On the drive home, she devoured the booklets Chloe had given us. Leaning back in her seat, one leg casually folded over the other, flipping pages with the same calm, predatory interest she had shown in the boutique. Every few pages, she’d make a sound, quiet but unmistakably aroused.

A soft, delighted “ooh…”

A breathy, pleased “ahh…”

Sometimes a low, contemplative hum.

Then a whisper meant entirely for herself, but one she knew I’d hear:

“Oh really…?”

“Mmm… that’s clever…”

“God, that’s going to hurt so nicely…”

And occasionally a thrilled, almost disbelieving little, “Wow…”

Her voice alone made my cock throb painfully against the inside of my trousers.

At one point, she shifted in her seat, crossing her legs again, and I heard the faint rustle of the lingerie bag between her feet, the lingerie she was going to put me in.

The vivid crimson panties.

The stockings.

The bra I’d held like a trembling idiot in front of strangers.

The cage sitting on top of the dildo, waiting.

She turned a page and inhaled sharply, biting her lip.

“Oh… oh, this part,” she whispered, fanning the booklet lightly as if to cool herself down. “This is going to make you absolutely whimper.”

I swallowed hard, unable to respond.

She kept reading.

More pages. More sounds.

“Mmm… that’s so deep…”

“Oh god… they recommend daily stretching.”

“Ooh… that’s big.”

“Mike… this position is going to turn you inside‑out.”

I could feel her looking at me sometimes. The slow, smug glide of her gaze over my lap, watching the way I shifted in my seat, trying to discreetly adjust myself without touching my aching erection. She didn’t miss anything.

EDUCATION

She flipped to another section, hummed thoughtfully, then laughed under her breath. “Oh my god. They even include porn categories to ‘accelerate submissive conditioning.’” She skimmed the list, her lip curling in amused delight.

“Let’s see… edging discipline videos… feminisation fantasies… sissy instructional clips…”

A pause.

A pleased exhale.

“Oh, and of course, strap‑on training. With tutorial dialogue.”

She looked at me, eyes glittering.

“They want you to watch things like this before I use the strap, just to ‘set the mood.’”

She tapped another heading. “And here, ‘Suggested options for submissive mindset reinforcement’… Mike…” She giggled. “These are filthy.”

She read a few aloud:

“‘Holding your partner’s hips while being taken.’

‘Maintaining eye contact in the mirror.’

‘Practising verbal responses such as yes ma’am, deeper, and please don’t stop.’”

She placed a hand lightly on my thigh, nails grazing just enough to make my breath catch. “Oh, sweetheart, you’re going to watch all of this for me. Over and over. Until just hearing a woman say strap‑on makes your knees weak.”

She flipped the page again, settling comfortably back into her seat, and murmured another soft, hungry “mmm…” as if she were reading a recipe she couldn’t wait to try.

A page in the next booklet must have caught her attention, because she suddenly went quiet, then murmured, almost dreamily: “…long‑term chastity recommendations…?”

She read more, her eyebrows lifting, then settling into a fascinated, wicked smirk.

“Oh my god… they have entire sections on keeping you locked for days… weeks… even months.”

Her voice softened into something dangerously thoughtful. “Honestly? I could get used to that. You walking around in pretty little panties, caged… needy… dependent… so desperate you whimper if I even brush your thigh.”

She tapped a line with her fingernail, slowly.

“Listen to this,” she murmured, tracing the paragraph with a fingertip. “Over time, the body adapts to being denied… erections weaken… some men even shrink a little from disuse.” Her eyes flicked to mine, bright and teasing. “Isn’t that something?”

I swallowed hard, my cock twitching in response to the thought.

She leaned back, still reading, her voice dropping to a hushed, intimate murmur.

“And it gets better,” she said. “The cages can be made smaller, tighter, as the man becomes more compliant. Over time, you can even use something called an inverted cock cage…” She held her fingers in a small curve. “…it presses the penis inward. Soft, tucked, almost hidden.”

My pulse jumped at the mental image.

“And the best part,” she continued, her eyes gleaming, “is that once the man’s completely adapted, wearing these… he looks natural, beautiful, even in panties.” She tilted the booklet toward me, her lips curling with a sly, predatory smile. “Like this isn’t unusual at all. The photos… the guys actually looked normal. You wouldn’t even notice anything’s different if you didn’t know.”

Her words sank deep, each one a tether pulling me lower into desire and humiliation. She leaned back in her seat, satisfied, folding the booklet on her lap.

“It’s meant for men who’ve surrendered completely,” she added softly, her voice thick with admiration and amusement. “Ones who don’t really… need to be a man down there anymore.”

She didn’t touch me. She didn’t need to. Her voice, her eyes, her calm ownership, it was enough.

“You’d be so pliant, sweetheart. So eager to please. And I’d hold the key whenever I wanted.”

My breath hitched.

She noticed.

Of course she did.

And I just drove.

Still hard.

Still leaking.

Still helplessly, hopelessly hers.

PREPARING OURSELVES

That night felt like a ceremony.

We showered together first, warm water running over us as we took turns gently scrubbing each other—smiling, giggling, letting our hands linger just a little too long. When it came time for the anal douches, a strange mix of nerves and anticipation fluttered through me. I had never done anything like this. She showed me how to fill it, how to relax, how to clean myself out properly. She stood behind me as I bent forward, rubbing my back reassuringly while I flushed myself out. It was intimate… vulnerable… unexpectedly arousing. Especially when she presented herself for me to return the favour, with the quiet promise of what the night would hold.

Afterwards, Sue suggested we take a little extra time to get ready properly. It wasn’t just about being clean; it was about feeling prepared, focused, feminised. She laid out a few things beside the sink: cream, a fresh razor, shaving foam, and a soft towel, then smiled at me through the mirror.

“Let’s make this neat,” she said gently. “A clean start.”

The words were simple, but her tone made them feel ceremonial. She guided me through each step as if it mattered, positioning me just so, legs open, cheeks parted, giving her full access as she worked. The faint scent of shaving cream filled the air; the steady sound of running water softened everything else. We didn’t speak much. We didn’t need to. What mattered was her calm assurance, the quiet focus, and the strange combination of comfort and exposure that came with letting her lead.

When we were done, Sue dried her hands and smiled at me. “Better,” she said softly. “Now you look like you want it.”

There was no teasing, just certainty. And that alone made my pulse quicken again.

COCK CAGE

Sue sat on the edge of the bed, the small, polished device resting in her hand like a question. “Let’s see how this works,” she said lightly, though her voice carried purpose.

I stood there, pretending uncertainty, while she examined it with curiosity rather than embarrassment. Her focus was practical, almost clinical, but her composure made it more disarming. She tried to assemble it, frowning slightly as she tested the fit.

“Hmm,” she murmured. “Trickier than it looks.”

First, we chose the base ring from the three provided, settling on the middle size. She attempted to fit it herself, but my involuntary squirms as she handled my balls turned the process clumsy enough that I ended up helping… carefully.

She then picked up the cage itself, the head of my cock already filling it completely. After studying it for a moment, she simply pressed it toward my groin; my shaft yielded under the pressure until the cage and ring aligned neatly, almost like it was being swallowed into place.

I offered faint suggestions, careful not to sound too knowledgeable. I knew exactly how it should go, of course, too well, but this wasn’t the moment to reveal that. My fingers joined hers only when she paused and looked up expectantly, the silence between us weighted with unspoken truths.

Next came inserting the barrel lock: notoriously fiddly, as I well knew. She struggled to line it up. I continued to feign inexperience, despite my private collection at home, and finally offered a “helpful” hand, guiding it into place.

When the lock clicked shut, she exhaled softly. “There,” she said, satisfied. “Now we can move on.”

DRESSING UP

Then came the lingerie.

We stepped out of the bathroom, towelling off, and she handed me the crimson lace set we’d bought. Stockings, suspenders, and silky pieces folded with care. Matching sets: hers and mine. She slipped into hers effortlessly, every movement confident. I fumbled, the air thick with nervous anticipation and something harder to name: the awareness that she was watching, assessing, delighted.

When I stepped toward the mirror, my face blazed. She looked radiant. I looked… absurd. And yet the sight of myself, lace hugging my hips, a bra shaped by soft inserts, and my caged bulge pressing against the panties turned me on more intensely than I expected.

She stepped behind me, wrapped her arms around my waist, and kissed my neck. “Look at you,” she whispered, meeting my eyes in the mirror. “My pretty little virgin… all dressed up to be fucked.”

I whimpered.

SETTING THE SCENE

Back in the bedroom, we pulled back the covers and lay side by side in our matching lingerie, streaming pegging porn on the TV. The room filled with moans, the slap of flesh, bodies surrendering on-screen. She spooned me from behind, one hand slowly stroking my ass through the silk panties, her fingers occasionally slipping under the waistband to tease the crease of my cheeks. Her breath was warm against my ear; her other hand toyed lazily with my nipples under the flat bra cups, mocking the lack of real curves.

She nuzzled the back of my neck and murmured, almost conversationally, “Tonight’s special, isn’t it?”

I nodded, my breath shaky. “Yes… It is.”

“Mmm.” She kissed my shoulder. “Then we should film it.”

Before I could process that, she reached across me, grabbed both our phones from the bedside table, and unlocked them with quick, decisive taps.

Her control.

Her idea.

My instant obedience.

“Here,” she said, placing my phone on the dresser angled at the bed. She positioned her own on the bookshelf opposite, adjusting each one until the lenses captured the whole space: the bed, the lingerie, the toys, and me.

I swallowed hard as she stepped back to admire her setup, hands on her hips.

“Perfect,” she said softly. “We’ll get everything. Your face… your reactions… your little moans when I push too deep.”

Then, almost as an afterthought, almost to herself, she added: “Maybe I’ll show the videos to Chloe.”

My heart lurched. “W-what?”

She smirked, sliding back into the bed behind me, her hand gliding between my thighs.

“Mmhmm. She’d appreciate the technique. And she did spend so much time helping us today.”

She paused, then laughed quietly.

“Maybe even the sales assistants… they already saw half our secrets anyway.”

My cock twitched violently at the thought, at her tone, at how casual she made it sound, like it was already decided.

She squeezed my nipple through the bra, hard enough to make me gasp.

“Relax,” she whispered. “I haven’t decided yet.”

Her hand drifted lower, cupping me through the panties. “But I love having options.”

Her words, the cameras running, the porn echoing in the background, all of it wrapped around me like a collar. And I melted back into her, trembling, helpless, waiting for her next move.

If you’d like, I can continue straight into how she gets the first recording started, positioning you, giving you orders, making you perform for the camera as much as for her.

“See that guy on the screen?” she whispered. “That’s you. That’s exactly what you’re going to look like tonight.” My cock leaked into the lace despite the cage.

When she finally rolled off the bed, I watched her walk across the room toward the harness and dildo kit. My mouth went dry. She stepped into the harness like she’d worn it for years, tightening the straps across her hips with a confident snap. Then she chose the smallest dildo, still intimidating, and clicked it into place.

“On your knees,” she said, her voice lower now, charged with power. “Let’s see how well you suck cock.”

I knelt in front of her, wearing my panties, bra, suspenders, and stockings, every bit of humiliation visible. She placed a hand on the back of my head and guided the silicone tip to my lips.

“Open up, sweetheart. Wet it properly. That cock’s going inside your ass.”

I obeyed. I wrapped my lips around the shaft and sucked, mimicking the submissive boy on the screen. She moaned theatrically, fingers sliding through my hair as she gently thrust. “Look at you,” she murmured. “You’re perfect for this.”

When she was satisfied with my worship, she had me lie back on the bed. She placed a pillow beneath my hips, then gently pulled my legs up and back, exposing me completely.

“I want you to watch,” she whispered. “I want you to see the moment you lose your virginity.”