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--
I giggled. "No Ryan. Sorry I can't do that." I dismissed the suggestion easily.
Earrings? Not a chance.
"Mmmm...is that right?" He kissed me again, deeply. I whimpered into his mouth and pressed into him.
He didn't push it further at that moment, and we settled into a pool lounger. I cuddled up against him, content. Soon after, Princess came out and settled in, cuddling up on the other side of Ryan.
She locked eyes with me. "Told you that you'd do great, baby." She winked.
I blushed, burying my face in Ryan's chest.
Listening to Ryan chuckle, I closed my eyes, choosing not to respond and relaxing into him instead. The cool air against my skin together with the heat radiating from Ryan felt incredible. I felt so calm, my mind going blank.
I wasn't sure if I dozed off, but I came to when I felt my hand being pulled down. Without opening my eyes, I realized Princess was pulling my hand down...under the hem of Ryan's trunks.
My heart began beating faster. I didn't mind though. My hand closed around Ryan's shaft and I began gently massaging him as Princess focused on his balls.
I tipped my head up, my eyes still closed, and found Ryan's lips waiting for me. I moaned into him, stroking him faster.
Princess slowed my hand down then interlocked her fingers with mine. Together we were able to encompass his entire girth - something I couldn't do with one hand alone.
As one, we pleasured Ryan smoothly, excitedly. I sucked on his tongue, whimpering as he gripped my ass hard. The calm and smooth romance and intimacy was incredible. I wasn't performing. I wasn't pretending. I wasn't nervous.
This felt natural. This felt right.
Ryan pulled his mouth off mine and I moved to kissing his neck.
"Princess." Ryan said. "What do you think of Janie getting her ears pierced?"
I kept kissing his neck, stroking his increasingly hard cock.
"Oooo...I love that idea."
"Don't you think she'd look good?"
"Absolutely. I could take her to a good place for it."
Their words sunk in. I kept sucking on Ryan's neck as he ran a finger along my ear, making me shiver.
"Janie?" Ryan asked me.
I tried to avoid answering, moving to kissing down his chest, wanting to meet my hands at his incredible manhood.
"No. Come here baby." Ryan said. "You've already been fed. It's Princess's turn."
Princess giggled and I felt her moving down his body. She pulled off my hand and replaced it with her mouth, pulling down Ryan's shorts and taking him deep. I moaned at the sight, jealous.
Ryan turned up my chin so I looked up at him, my hand still resting on his abs, itching to join Princess.
He continued to run a finger along my ear, then he squeezed my earlobe, making me gasp.
"Will you do it, Janie? For Daddy?"
I looked between his eyes, to his lips again. Was it even possible to resist this perfect man? Undr his gaze, my resolve melted away. "Okay..." I almost called him Daddy like I knew he wanted me to. But something held me back. Some shred of dignity remaining from before I'd licked Ryan's cock like a lollipop.
But I did agree. I'd do it for him. And I was rewarded by Ryan pulling me up so I straddled his chest and kissed me hard, his hands squeezing my ass as Princess sucked him off right below it.
We continued kissing and sucking like that until finally, Ryan exploded into Princesses mouth. She choked and pulled her mouth off his cock, allowing a few hot jets to land on my back. I trembled as I climaxed on top of Ryan in my little blue bathing suit, which still covered all of me even hard. It was at least my 4th of the day.
Ryan told Princess to clean me off with her tongue, and told me I could lick off some of my own mess that had gotten on Ryan's shoulders and chest. We each obeyed happily.
----
I picked up Princess the next day. I worried what Caroline would think of all this. Would she still be supportive of something so...permanent? I wore a tight black shirt and grey yoga pants Ryan had given me. On a whim, I sent him a pic of my outfit. "Thanks for the clothes!" I texted under the pic.
As we drove to the jewelry store, he replied. "Fuck yeah. You look hot, babe. Send me a pic once you've got some bling on that beautiful ear."
I smiled, texting him back. "Okay" with a kiss emoji. I stared at the kiss emoji for a second before putting my phone in my pocket.
We entered the store. I felt exposed yet oddly exhilarated. The cool air conditioning raised goosebumps on my bare back.
Soft classical music played in the background, creating a soothing atmosphere. Princess confidently approached the counter, her high heels clicking on the polished floor.
"We're here for an ear piercing," she told the attendant, placing a hand on my lower back. I felt a flutter in my stomach at her touch.
The attendant, an attractive woman in her thirties with sleek blonde hair and impeccable makeup, smiled warmly at us. "Of course! Right this way."
She led us to a small, private room in the back of the store. A comfortable-looking chair sat in the center. Various piercing tools and jewelry options were neatly arranged on nearby shelves.
"I'm Melissa," the technician introduced herself. "Which of you lovely ladies will be getting pierced today?"
Princess gently nudged me forward. "This cutie right here," she said with a grin.
Melissa's eyes roamed over me appraisingly, lingering on my exposed back and the way my yoga pants hugged my curves. "Wonderful," she said, her voice warm and enthusiastic. "Have a seat, girl!" Though Ryan and Princess had been addressing me as a girl for days, this was the first time a stranger had done so. I knew it should have repelled me. But...well it made me feel good. Really good.
I smiled at her as I settled into the chair. But then my heart began to race. The reality of what I was about to do hit me full force. Princess must have sensed my nervousness because she took my hand, giving it a reassuring squeeze.
"Now," Melissa said, pulling on a pair of latex gloves, "let's choose your starter earrings. We have a lovely selection of studs."
She presented a tray of gleaming options - delicate pearls, sparkling cubic zirconia, and simple silver balls. My eyes were drawn to a pair of small, silver studs.
"Those," I said softly, pointing.
"Excellent choice," Melissa smiled. "They'll look beautiful on you." After setting up for a few minutes, she approached with the piercing gun, and I instinctively tensed. God...what was I doing? Was this insane? It kinda felt insane!
Tensing more, I almost stood up. But then Princess's hands were on my shoulders, holding me down. "You're going to look so sexy, Janie." She whispered.
Sexy...
"Deep breath," Melissa added soothingly. "This will be quick."
She lined up the gun with my earlobe. I inhaled sharply as there was a loud click, followed by a sharp pinch. I whimpered, feeling my eyes tear up. It hurt!
Princess leaned in close, her breath warm against my ear. "Ryan is going to love this," she whispered. "He'll think you look so hot with pierced ears. His little Janie."
A shiver ran down my spine at her words, but I still cringed as Melissa brought the gun to my other ear. Again Princess put her hands on my shoulders, preventing me from wimping out.
Click. Pinch.
Ten minutes later, after Melissa had put in the studs and I'd calmed down, Princess took a picture for Ryan. I smiled, and happily sent it to him a few minutes later.
--
I stood in front of the mirror after showering that night, transfixed at the sight of my newly pierced ears. I couldn't keep my mind from running wild. The earrings did look beautiful. I looked beautiful. Ryan was so right.
But could I look more beautiful for him? No...I shouldn't...
I turned and opened Caroline's make-up drawer, my heart beating face. Before I could change my mind, I began applying Caroline's makeup to myself.
I quickly realized, however, that I couldn't do this quickly. It was hard! I ended up watching about an hour worth of youtube videos - instructions from a bunch of pretty teenage influencers.
Finally, I pulled away, looking at myself wide-eyed.
The transformation was stunning. My eyes, rimmed with dark liner and smoky shadow, seemed larger and more alluring. Long, curled lashes framed them perfectly, drawing attention to their depth. A soft blush gave my cheeks a rosy glow, accentuating my cheekbones in a way I'd never noticed before. My lips, painted a soft pink, looked fuller and more inviting.
The silver studs in my newly pierced ears caught the light, adding a delicate sparkle that complemented the makeup beautifully. I turned my head from side to side, admiring how they looked from different angles. They made me feel pretty, feminine... desirable. Inspired by an idea, I pulled a towel around my chest tightly, pressing my breast...my pecs together. I giggled...I had cleavage!
I ran my fingers through my hair, tousling it slightly to frame my face. The overall effect was softer, more alluring than I'd ever looked before. For a moment, I barely recognized myself - but in the best possible way. I felt beautiful, confident... sexy.
Impulsively, I grabbed my phone and snapped a few selfies, pouting and smiling at the camera. Before I could overthink it, I sent the best one to Ryan with the caption "How do I look, Ryan?"
My heart raced as I waited for his response. When my phone buzzed a few minutes later, I eagerly opened his message:
"Gorgeous, baby girl. You're a natural beauty. Can't wait to see you again soon."
A warm flush spread through me at his words. I felt giddy, validated... and incredibly turned on. I was about to reply when I heard the front door open.
"Jamie? I'm home!"
Caroline's voice jolted me back to reality. Panic set in as I realized I was still wearing full makeup and my new earrings were clearly visible. I scrambled to find something to change into, seeing only a pink gym outfit from the fe-male line that Ryan had given me. I threw it on.
Taking a deep breath, I stepped out of the bathroom to greet my wife.
Caroline's eyes widened as she took in my appearance. "Jamie? What... what is all this?"
I shifted nervously, suddenly very aware of how I must look to her. "I... I was just experimenting a little. Um...to keep Ryan happy like you asked."
Her gaze hardened as she noticed the studs in my ears. "Are those... did you get your ears pierced?"
I nodded, reaching up to touch one of the earrings self-consciously. "Yeah, I...."
Caroline's face darkened. "Jamie, we need to talk. Now." Her voice was tight with barely controlled anger.
She grabbed my arm and led me to the living room, practically pushing me onto the couch. I felt small and vulnerable under her intense gaze as she paced back and forth in front of me.
"I learned a lot on this trip," Caroline began, her voice strained. "And today I heard things that change everything."
She stopped pacing and fixed me with a hard stare. "I spent a considerable amount of time with the CEO - Ryan's father. We had several long conversations. But today, on the plan home. What he told me... Jamie, it's bad. Really bad."
My heart raced as I waited for her to continue. What could Ryan's father have said that had Caroline so worked up?
"According to him, Ryan is nothing but a no-good womanizer," Caroline spat out. "He's been causing problems in the company for years. Do you know how many people have been fired because they got involved with him?"
I shook my head mutely, a cold dread settling in my stomach.
"At least a dozen," Caroline continued, her voice rising. "A dozen people lost their jobs, their careers, because they couldn't resist that... that boy's charms. And now he's set his sights on me." Her eyes looked me up and down. "On us."
She ran a hand through her hair, visibly distressed. "Jamie, I'm scared. I'm scared for my job, for our future. We can't keep doing this. We can't keep playing Ryan's games."
I opened my mouth to speak, but Caroline cut me off. "No, listen to me. We're done. We're cutting all contact with Ryan, effective immediately."
She stormed off to our bedroom, returning moments later with an armful of clothes - it looked like every article from the fe-male line that Ryan had given me. Without a word, she marched to the trash can and dumped them all in. I felt my heart ache at the sight. Those clothes...those incredible outfits...
"Caroline, wait-" I started, but she whirled on me.
"No, Jamie. This ends now. I'm blocking his number on both our phones. We're not seeing him again, we're not talking to him again. It's over."
I watched helplessly as she grabbed our phones, quickly deleting Ryan's contact and blocking his number. The finality of her actions left me feeling hollow.
Caroline's expression softened slightly as she sat down next to me on the couch. "Look, I know... I know things have been confusing lately. For both of us. But we need to put this behind us. All of it."
She reached out, gently touching one of my newly pierced ears. "If you can forget about what I've done - the flirting, the...worse stuff - I can forget about this. About the clothes, the makeup, the... changes. About you kissing him. We can start fresh, Jamie. But only if we cut Ryan out completely. Do you understand?"
I nodded slowly, my mind reeling. God she didn't know. Didn't know how far we had gone. Part of me reeled from it all - the clear-eyed realization of what I had done. Of the path I was going down, all for this 18 year old boy.
No...18 year old Man. Whatever else he was...I thought, picturing his long thick cock...he was not a boy.
That week, I tried to be normal. I really did. But everything felt off, like I was living someone else's life. My clothes felt itchy, loose and dull compared to the vibrant, form-fitting outfits Ryan had given me. I caught myself staring longingly at the spot in the closet where they used to be.
In bed with Caroline, I felt disconnected and awkward. When she reached for me, wanting to rekindle our intimacy, I found myself unable to respond. My body, which had been so alive and responsive with Ryan, now felt numb and uncooperative.
"It's okay," Caroline soothed, stroking my hair as I turned away in embarrassment. "Another night. You're just tired."
But as the days wore on, I continued to feel like a stranger in my own skin, uncomfortable and out of place. The mirror became my enemy and my obsession. I'd stare at my reflection, trying to resolve that this is who I was. I was James. Jamie for short.
During the day, I'd catch myself daydreaming about Ryan - his confident smile, his commanding presence, the way he made me feel so desired and beautiful. Then I'd shake myself out of it, guilt and confusion warring inside me.
I wanted to reach out to him desperately, but Caroline had deleted his number and blocked him on our phones. I couldn't find him on social media. It was as if he'd vanished completely, leaving only memories and longing in his wake.
Part of me, a big part, needing something to cling to. Something physical. Just as a reminder. So I took to wearing the silver stud earrings at night, careful to remove them each morning before Caroline woke. It was a small act of rebellion, a tiny connection to the person I'd been becoming. As I'd insert them each night, I'd hear Ryan's voice in my head: "Good girl, Janie." The memory would send shivers down my spine and make my heart race.
Caroline, for her part, seemed determined to pretend nothing had ever happened. She threw herself into work, coming home late most nights. When she was home, she'd chatter about mundane things - office gossip, what to have for dinner, plans for the weekend. It was as if the past few weeks had been erased, leaving only the hollow shell of our former life. She didn't mention Ryan and I got the impression his internship rotation had moved on to another group.
I tried to engage, to be the husband she wanted and expected. But every attempt felt forced and false. I couldn't shake the feeling that I was playing a role, one that no longer fit.
One evening, about a week after our confrontation, Caroline came home with a nervous look.
"Jamie, honey. Friday is my work dinner. You know - the end of summer one they have each year?"
I nodded, remembering it was a fancy affair.
I looked at her, not daring to ask the first question coming to my head.
She still knew. "I don't know if he'll be there, Jamie. I hope not."
I nodded, looking away, blushing.
She sat down, holding my hands. "Jamie. If he is. We need to watch ourselves extremely carefully."
"I know..." I replied quietly.
"The CEO can't find out anything happened. But we also can't piss him off and make a scene. Jamie, this dinner is important. To me. To us."
"I know, I know." I insisted. "Don't worry. We'll be fine." I squeezed her hands back and she seemed to relax.
"I feel like he's going to try something, Jamie. Just to mess with us. Or in revenge. He's so used to getting what he wants."
"Yeah..." I replied. I still hadn't told her everything I'd done. I thought she might suspect, but she hadn't said anything.
"We can't fall for his manipulations. Promise me, Jamie. It's so important. I'm right on the edge of something big here."
"Yeah..of course. I mean no way will we fall for it, babe." I looked at her in the eyes, then attempted to give her a forceful kiss.
It did not feel forceful. It did not FEEL at all.
But still she seemed satisfied, nodding her head resolutely at me. "Thanks, Jamie."
--
The rest of the week passed in a blur of nervousness and...deep down...excitement. I suppressed that feeling though. Other than wearing the earrings, I was determined to be true to Caroline.
The night of the dinner arrived. I wore a turquoise button down shirt and khaki pants. Caroline wore an elegant red dress. She had had her hair blown out and it was sleek and wavy. I told her she looked amazing, but the truth was it was at least one size too small. She just didn't have the figure she once had.
As we walked into the ballroom holding hands (45 minutes after it started - Caroline believed in being fashionably late), I scanned the hall unconsciously, automatically.
I couldn't see him.
Caroline began talking to a coworker and I told her I would grab us a drink. At the bar, I kept looking around. No, he wasn't there.
I told myself I was relieved. And indeed my heart rate slowed significantly. But I also recognized the part of me that was immensely disappointed.
That was okay. I thought. It was part of moving on. As the dinner proceeded, we found ourselves only one table over from the CEO. Caroline was very excited about this, and spoke to our table mates excitedly, almost manically, as I sat mostly quiet, smiling and nodding along.
Then I froze, my glass of champagne halfway to my lips. Ryan had just walked in, and the sight of him took my breath away.
He looked incredible. Even through the perfectly fitting tux you could tell he was muscular. The jacket hugged his broad shoulders and tapered down to his narrow waist, accentuating his V-shaped torso. The crisp white shirt underneath strained slightly against his chest, hinting at the defined pecs beneath. His pants were perfectly tailored, clinging to his muscular thighs and... I forced my eyes back up, feeling a blush creep across my cheeks.
I was so fixated on him I almost didn't notice her. I couldn't believe it.
It was the barista from that coffee shop at the end of our runs. She was stunning in a black strapless gown that complemented her olive skin perfectly and accentuated her generous curves. Her dark hair was styled in elegant waves, and elaborate diamond and silver earrings sparkled at her ears. She looked delighted to be there. I felt a rush of anger and jealousy. Just like at the coffee shop the words rushed to my head - That bitch! Who was she to be here with him?