This is a follow up to Money Troubles - Chapter 1.
If you have not read that, please take the time to read it here:
The next three days stretched into an eternity of anticipation and humiliation. Each morning I’d wake with a knot in my stomach, and each evening I’d fall asleep with the same knot twisting tighter.
On Wednesday, Stacey cornered me in the bathroom while I was brushing my teeth.
“You know,” she said, leaning against the doorframe with her arms crossed, “Tom probably expects a smooth, proper lady for Saturday.” Her eyes traveled down my body with a critical gaze. “All that body hair won’t do.”
I spat toothpaste into the sink. “What are you talking about?”
She laughed. “Don’t be dense, Trey. You can’t show up hairy like a gorilla in a dress. You’ll need to shave.”
“Absolutely not,” I said, turning to face her. “There’s no way I’m shaving my whole body.”
Her expression hardened. “Really? Because five thousand dollars says you will. Or would you prefer I call Tom right now and cancel? I’m sure he’ll understand that you’re too manly to go through with it.”
The threat hung in the air between us. I knew she would do it too. With a sigh of defeat, I nodded. “Fine. But I don’t know how to shave everything properly.”
A wicked grin spread across her face. “I’ll help you.”
That evening found me in our shower, steam clouding the glass as Stacey entered, with a razor in hand
“First, the legs,” she said, lathering them with shaving cream. “Make sure to go against the grain for the closest shave.”
Her hands glided over my calves, the razor scraping away hair I’d had since puberty. I watched in a strange detachment as my legs transformed, becoming smooth and foreign. The sensation was both intimate and clinical.
“Armpits next,” she instructed, raising my arm. “These are tricky. Don’t press too hard or you’ll cut yourself.”
By the time she finished, I felt raw and exposed. But she wasn’t done yet.
“Bend over,” she commanded. When I hesitated, she added, “Trust me, you don’t want any surprises for Tom if things get... intimate.”
Humiliation burned through me as I complied. I felt her spread my cheeks, her fingers cool against my skin.
“You have some peach fuzz around your hole,” she said matter-of-factly. “We’ll get that too.”
The razor there was the worst violation, making me flinch with every careful stroke. When she was done, she patted my skin dry with a towel.
“There now,” she said, standing back to admire her work. “Perfect. Smooth as a baby’s bottom.”
Thursday brought new torments. Stacey found me in the living room, scrolling through job listings on my laptop.
“You know,” she began, “walking in heels takes practice. You should probably start.”
I shook my head without looking up. “No way.”
She sighed dramatically. “Don’t be difficult. You’ll embarrass yourself on Saturday if you can’t walk properly.”
“I don’t own any heels,” I countered, thinking I’d found an out.
A glint appeared in her eyes. “I’ll buy you a cheap pair if you ask nicely.”
My pride warred with my desire to end the conversation. “Fine. Will you please buy me some heels?”
She shook her head, tsking. “Not good enough. Ask again, like you really want your own pair of high heels.”
Heat flooded my cheeks. “Stacey...”
“Like you mean it, Trey. Or I’ll assume you’re backing out of the whole arrangement.”
I swallowed hard, my throat tight. “Stacey, would you please... buy me a pair of high heels? My very own pair?”
A triumphant smile spread across her face. “Of course, dear. Anything for my pretty girl.”
Friday night, I was curled on the couch when Stacey sat beside me, remote in hand. “Let’s watch something,” she suggested, her tone unusually sweet.
A flicker of hope ignited in me. Sometimes we watched porn together before sex, and it had been weeks. Maybe tonight...
She navigated to a streaming site I didn’t recognize, and my excitement soured as the title appeared: “First Time Lessons: Trans Edition.” The scene opened with a beautiful woman coaching her transgender partner on giving oral sex to a man.
“What is this?” I asked, my voice tight.
“Educational material,” Stacey replied casually. “You might need these skills on Saturday.”
I started to protest, but she cut me off. “Don’t pretend you’re not interested.” She gestured to my crotch where, despite my mortification, I was noticeably aroused.
The shame of my body’s betrayal was overwhelming. On screen, the woman demonstrated technique with a dildo, explaining in detail how to please a man.
“Maybe you should practice,” Stacey suggested,
“No way,” I said, shaking my head. “Absolutely not. This is insane.”
Stacey’s fingers danced across the remote, pausing the scene at the most compromising moment. “Don’t be such a child, Trey. Would you rather go into Saturday completely unprepared? Tom seems like the type who expects... expertise.”
The word hung in the air between us, heavy with implication. I could feel my heart hammering against my ribs, a frantic bird trapped in a cage of bone.
“Expertise?” I squeaked. “Stacey, this is—”
“—better than fumbling around like an idiot when some wealthy man expects you to know what you’re doing?” she finished, arching one perfect eyebrow. “Think of it as professional development.”
A strangled sound escaped my throat—part laugh, part sob. Professional development. Like this was some corporate training seminar.
“I can’t,” I whispered, the words barely audible.
Stacey sighed, then stood up. When she returned, she held the dildo from our bedroom—a silicone toy we hadn’t used in years, since before my job troubles had begun. She sat beside me again, close enough that I could feel the warmth radiating from her skin.
“Open up,” she commanded, her voice soft but firm.
When I didn’t comply immediately, her free hand came to rest on my jaw, her thumb stroking the line of my chin. “Trey,” she said, her tone dropping to that dangerous whisper that always made my stomach clench. “Remember Cancun? Remember how you kept asking until I said yes, even though I was terrified?”
My throat went dry. I nodded, unable to speak.
“Exactly. Now open up.”
Slowly, reluctantly, I let my lips part. The silicone felt cool against my tongue, foreign and invasive. I gagged instinctively.
“Breathe through your nose,” Stacey coached, her voice almost gentle now. “Relax your throat. Watch how she does it on screen.”
My eyes flickered to the television where the woman was demonstrating, her movements fluid and practiced. I tried to mimic her, my movements awkward and clumsy. The toy filled my mouth, pressing against my tongue, triggering a reflex to push it out.
“Good,” Stacey murmured, surprising me. “Now take a little more.”
I complied, my lips stretching around the silicone. Something shifted in Stacey’s breathing—something deeper, more resonant. I risked a glance at her face and saw her eyes had darkened, her pupils dilated.
“Like that,” she whispered, her fingers tightening on the base of the dildo. “A little more suction with your tongue... yes, just like that.”
Her breathing grew ragged as I continued, finding an awkward rhythm. The scene on TV played on, but my focus had narrowed to the sensation in my mouth and the changes in Stacey’s expression.
“That’s it,” she moaned, her voice thick with desire. “Take it all.”
Her hand moved from the base to the back of my head, her fingers tangling in my hair. She applied gentle but firm pressure, guiding me forward until the silicone hit the back of my throat. I gagged again, tears springing to my eyes.
“Shhh, relax,” she soothed, even as she held me there. “You’re doing so well.”
The contradiction in her actions and words sent a jolt through me. On screen, the woman was demonstrating how to deep throat, her movements practiced. Stacey began to mirror this, pushing my head down further with each movement.
“Fuck,” she breathed, her hips shifting slightly on the couch. “That’s... that’s really hot.”
Her moans grew louder, more frequent. I could feel the vibrations through the silicone, a strange connection between my mouth and her body. Her fingers tightened in my hair as her control slipped.
“Yes, just like that,” she gasped, her other hand moving between her legs. “Don’t stop.”
I felt her body tense, her back arching. Her grip on my head became painful as she pushed down one final time, holding me there as waves of pleasure washed over her. I could feel her thighs trembling against mine, hear the breathy cries that escaped her lips.
When she finally released me, I fell back against the couch cushions, gasping for air. My lips felt swollen, my jaw ached. I looked at Stacey, expecting to see triumph or satisfaction, but found only surprise etched across her features.
“Holy shit,” she whispered, her chest rising and falling rapidly. “I... I didn’t expect...”
She didn’t finish, but I understood. She hadn’t expected to be so turned on by watching me submit to her, by seeing me perform this act of surrender.
For a moment, we sat in silence, the only sounds our ragged breathing and the faint moans from the television. Then Stacey reached out, her fingers gently touching my swollen lips.
“Are you okay?” she asked, her voice softer than I’d heard in months.
I nodded, unable to trust my voice.
“Good,” she whispered, her thumb tracing the outline of my mouth. “Because I think... I think we need to practice more tomorrow.”
The look in her eyes held something new—not just dominance or control, but genuine desire. I felt a confusing mix of shame, humiliation, and something dangerously close to pride that I had pleased her.
As I went to bed that night, my body still tingling from the experience, I couldn’t shake the thought that something fundamental had shifted between us. And I couldn’t decide if I was terrified or thrilled by what might come next.
The morning light filtering through our blinds felt harsh, accusatory. My heart hammered against my ribs like a trapped bird. Saturday. The day of my... date. I paced our bedroom, bare feet sinking into the carpet, my hands trembling.
“You’re going to wear a hole in that rug,” Stacey’s voice came from the doorway. She leaned against the frame, already dressed in yoga pants and a sports bra, looking impossibly relaxed. “Calm down. It’s just one evening.”
“Calm down?” I whirled to face her. “Stacey, I’m about to go on a date with a man who paid me to dress up like a woman.”
She crossed the room, her movements fluid and confident. “And now you know how I feel every time you ask me to wear that tight red dress and six-inch heels to your company parties.” Her tone was teasing, not cruel. “Welcome to my world, pretty girl.”
Despite myself, I managed a weak smile.
“Come here,” she said, patting the edge of our bed. “Let’s do your nails. We don’t want to be scrambling when the car arrives.”
I sat, my hands resting on my knees. Stacey pulled out a small case of nail polishes, selecting a deep crimson. “Red,” she said, opening the bottle. “Always looks high-end. A little pop of color.”
As she carefully painted each nail, her touch precise and gentle, a strange calm settled over me. The quiet intimacy of the moment felt normal, domestic, despite the circumstances.
“You know,” she said, her focus on my thumbnail, “last night was... fun. Different.” She glanced up at me, her eyes soft. “You seemed more... yourself when you weren’t trying so hard to be the man in charge.”
I didn’t know what to say to that, so I just nodded.
“We should practice again when we’re done here,” she continued, finishing the last nail. “Help you get more comfortable.”
My stomach clenched at her words. Practice. What did that mean?
She seemed to read my thoughts. “I was thinking... maybe you should let me use one of my dildos on you. So you know what it feels like, just in case Tom wants more.”
Panic surged through me, hot and immediate. “No. Absolutely not.”
Stacey’s expression hardened slightly. “Trey, it would be better to experience it with me first than to be surprised by him.”
I shook my head, my nails still tacky with polish. “I can’t.”
She sighed, then a new idea seemed to strike her. “What about the small butt plug? The one I bought when you were pressuring me about anal?” Her voice was gentle but firm. “Just to see how it feels.”
The memory hit me like a physical blow. I remembered buying that plug for her, insisting it would help her relax and enjoy anal sex. The irony wasn’t lost on me.
After a moment of silence, I nodded. “Okay. But just the small one.”
Stacey’s face broke into a triumphant smile. “Perfect.”
Once my nails were dry, she led me to the bedroom. “Pull down your pants and bend over,” she instructed, her voice casual. “Palms on the bed.”
How had I gotten here? Less than a week ago, I was worrying about finding a job. Now I was about to let my wife insert a butt plug into me to prepare for a paid date with a man who had propositioned me in a lingerie store. The absurdity of it all made my head spin.
I complied, my bare ass exposed to the cool air of our bedroom. I heard the click of a lube bottle opening, then felt something cool and wet against my entrance.
“Relax,” Stacey murmured, her fingers tracing circles around my hole. The sensation sent shivers through me, my breathing growing heavy despite my anxiety.
Her finger slipped inside, slow and deliberate. I gasped at the intrusion, my body tensing instinctively.
“Shhh,” she soothed, moving her finger gently. “Just breathe.”
I felt myself responding, my cock beginning to stir against my thigh. The shame of my body’s betrayal was overwhelming, but I couldn’t deny the pleasure building within me.
Stacey noticed too. “Well, well,” she teased, her voice husky. “Someone’s enjoying this.” She added a second finger, stretching me gently. “Getting excited about your big date tonight?”
I couldn’t respond, my breath catching in my throat as she continued her exploration. Her fingers found that sensitive spot inside me, and I moaned despite myself.
“There we go,” she whispered, withdrawing her fingers. “Ready for the plug?”
The tip of the plug pressed against me, cool and smooth. I held my breath as Stacey applied steady pressure, my body resisting at first, then yielding to the intrusion. The silicone stretched me wider than her fingers had, a fullness that bordered on pain but hovered just at the edge of pleasure.
“Breathe out,” she coached, her voice low and hypnotic. “Let it in.”
I exhaled slowly, and with that release, the plug slipped past the tight ring of muscle, seating itself inside me. A wave of sensation washed through my body—intense, overwhelming, undeniably erotic. I collapsed forward onto my elbows, my breathing coming in ragged gasps.
My cock throbbed against my thigh, hard and demanding. The plug filled me completely, its base nestled against my cheeks, a constant reminder of its presence. Every shift of my weight sent jolts of pleasure through me.
“God,” I groaned, reaching down to stroke myself. I needed relief, desperately.
“Ah, ah,” Stacey chided, smacking my hand away. “None of that. You should save that erotic energy for Tom later.”
Her words sent another surge of humiliation through me, but the humiliation only intensified my arousal. I was leaking now, pre-cum glistening on the head of my cock.
I started to pull up my shorts, needing to cover my embarrassing state, but Stacey stopped me.
“No,” she said firmly. “You’ll wear panties instead. Tom expects a lady, and ladies don’t go commando.”
She retrieved a pair of black lace panties from her drawer—the same style I’d seen her wear countless times. The fabric felt delicate in my hands, impossibly feminine.
“Step into them,” she commanded.
I complied, my movements stiff and awkward. The lace caressed my skin as she pulled them up, the delicate fabric clinging to my curves. The crotch settled against my erection, creating a wet spot where my pre-cum soaked through. I could feel the plug shifting inside me with every small movement, a constant, maddening stimulation.
“There,” Stacey said, stepping back to admire her handiwork. “Perfect. You look... desirable.” Her eyes darkened as she took in the sight of me—smooth legs, painted nails, lace panties barely containing my arousal, with the base of the plug just visible between my cheeks. “Maybe I should be the one taking you out tonight.”
The thought sent another jolt through me, and I had to bite my lip to keep from moaning.
The plug remained a constant, intimate presence inside me. Every subtle shift of my weight, every breath I took, seemed to translate into a pressure against that sensitive spot deep within. Stacey and I tried to watch television, but I couldn’t focus on the screen. The clock on the wall kept drawing my eyes—3:17, 3:42, 3:58. Each passing minute felt like a countdown to my surrender.
“Adjusting to your new accessory?” Stacey asked at one point, her voice laced with amusement as she caught me shifting uncomfortably on the couch.
I glared at her. “Can I take it out now? Please?”
She shook her head, her expression unyielding. “Absolutely not. In fact, I think you should keep it in during your date.”
My stomach dropped. “What? All night?”
“Why not?” she said, her tone casual. “Consider it... preparation. Besides, it seems to be having quite the effect on you.” Her eyes flickered down to where my arousal strained against the lace of my panties.
I couldn’t deny it. The humiliation of our conversation, combined with the plug’s constant stimulation, had me achingly hard. “I can’t go out like this,” I protested weakly. “Every time I move... or sit down too fast... it...”
“It what?” she pressed, leaning closer. “Hits that special spot? Makes you want to moan?”
Heat flooded my cheeks. I nodded, unable to meet her gaze.
“Good,” she said simply. “Now, any predictions about what Tom might send over?”
I shook my head. “I have no idea.”
Stacey’s eyes lit up. “I bet it’s gorgeous. Designer label, of course. And I hope the heels are at least five inches. You’ll need the practice.”
As the clock ticked toward four, she studied me thoughtfully. “You know,” she said, tapping a finger against her chin, “I can’t keep calling you Trey while you’re all dressed up. That’s a boy’s name.”
My pulse quickened. “What are you talking about?”
“We need a proper name for tonight. Something feminine, but not too obvious.” She considered for a moment. “What about... Tiffany? No, too common. Brianna? Too young.”
Just then, the doorbell chimed through the house, making me jump. The sudden movement sent the plug pressing against that sensitive spot, and I had to bite back a gasp.
Stacey’s face lit up with excitement. “They’re here!”