OMG, I Got the Sweetest Email Ever!

So yesterday, I received the most heartwarming email from a lovely crossdresser named Steph and honestly, it had me giggling one moment and tearing up the next. But the real star? Her incredible wife, Lucy.

I’m still swooning over how supportive, cheeky, and absolutely fabulous she is. Here's what Steph wrote (shared with permission, of course):

Dear Miss Kate,

I've been following your blog for quite some time now, quietly on the sidelines. For the longest time, I’ve felt too nervous to reach out, until now. Something happened recently, something deeply personal that moved me so profoundly I felt compelled to share it with someone who might truly understand.

A little about me I'm 50 years old, married to the most wonderful woman in the world, Lucy. In our day-to-day lives, I’m just Matt. Average. Slightly overweight. I work in media. But when I allow myself to be fully seen and felt, I become Steph. That version of me, the real me, doesn’t often get to live out loud.

Life’s been stressful lately. Work is chaos, layoffs, poor decisions from leadership, and an overwhelming sense of instability. It’s been emotionally draining. I cry more often than I’d like to admit. Some days, I barely recognize the person I’ve become. I wrestle with feelings of inadequacy, loss, and guilt.

Through it all, Lucy has been my anchor. She's a nurse a literal angel in scrubs and even though she has her own complex journey in trying to understand and come to terms with my femininity, she’s remained by my side. We’ve had moments of pure, breathtaking connection. She has looked at me, dressed as Steph, and seen the person I wish I could always be. She has also looked at me with confusion, even pain. There have been times when her acceptance has shone brightly, and others when resentment, anger, and grief have surfaced. I can’t blame her. It’s not been easy for either of us.

One of the hardest parts for me to admit is how aging has affected our intimacy. Lucy likes to be taken, to feel wanted, to be claimed. And the truth is, I feel like I’ve failed her. As I’ve aged, my body has changed. My ability to perform in the ways she once knew and needed has faded. Erection issues, especially when I'm not presenting as Steph, have become more common. Paradoxically, the only times I feel physically aroused or capable is when I’m wearing lingerie or expressing my feminine self. That truth brings a heavy shame I don’t quite know how to carry.

Sometimes I see it in Lucy’s eyes that quiet sadness, the lingering doubt. Does he still desire me? Does he still love me? And I do. God, I do. But I also know my love doesn’t always reach her in the form she craves most. I hate that. I hate feeling like I'm letting her down.

Still, we keep trying. We talk, we cry, we even laugh. Our love endures, even through the cracks. And recently, something shifted between us in a way I can’t fully explain but it gave me hope. It made me believe that maybe, just maybe, there’s a space for both of us to exist fully, truthfully, together.

And one of those moments? It happened last weekend. Lucy planned a surprise weekend getaway for us, just the two of us. She booked a 5-star hotel in the city and told me, quite casually, "Pack your wigs, breastplate, and some nightwear for Steph, but nothing else." I was curious and a little nervous, but mostly excited!

Once we arrived and dropped off our bags, she took me shopping! Yes, shopping, darlings! Lucy picked out a gorgeous pencil skirt, a dreamy blouse, matching lingerie, and the most divine pair of heels and handbag to go with it. I was honestly floating on air. 

At one point, we were sipping lattes in a cozy café and she playfully asked me to point out men I thought Steph would fancy. I blushed so hard I could’ve melted right into my coffee. It was cheeky, intimate, and just… magical.

Back at the hotel, Lucy poured us wine and laid out all the beautiful things she had bought. Then she looked at me and said, “Off to the shower, missy! Come out fresh, sparkly, and ready wig and breastplate on.”

So I did. My little heart (and other bits 😳) were fluttering as I stepped into that warm water, shaving, cleansing, and prepping myself. The silicone of my breastplate felt heavy but affirming, and I couldn't help but giggle at the way my pert little boobs bounced as I moved. Of course, I hated my tummy in the mirror I am a size 14 UK (I so want to slim down to a UK 10), but wrapped in a towel and with freshly brushed hair cascading down to my shoulders, I stepped out to find Lucy sitting on the bed, going through makeup like a pro.

She did my face so beautifully soft smoky eyes, glossy lips, and then... nails! For the first time ever, she glued on a full set of French tips. Looking at my hands, I barely recognized them. They were hers. They were Steph’s.

She helped me into the gorgeous black basque and matching thong both by Rosie at M&S and I nearly swooned as the delicate fabric slid up my freshly shaven legs. I felt adored. Feminine. Seen. She adjusted the straps of my basque, gently tweaked my nipple with a giggle, and whispered, “This only works if you play your part, sweetheart.”

I melted.

She clipped my stockings in place and handed me the rest of the outfit the blouse, the skirt and soon enough I was slipping into my heels and looking at myself in the mirror. Was I perfect? No. But in that moment, I felt like a woman. A real one. Full of longing, softness, and quiet confidence.

Then Lucy did something cheeky. She sat me at the desk, opened my laptop, and said, “Go on, read your favorite blogs. Imagine being one of the girls in those stories.”
So I did. False nails clicking on the keyboard, lips tingling with gloss, I was lost in a dreamy daze. 

Until...

Lucy stepped out of the bathroom, and for a moment, I forgot how to breathe. She was wearing a tailored, charcoal-gray trouser suit that hugged her in all the right places, sharp lines, clean edges, pure power. Her hair was slicked back into a tight, deliberate style that framed her face with striking elegance. There was a calm dominance in her expression, in the way she carried herself, effortless, commanding, unmistakably in control.

My heart raced. My legs moved on their own as I stood up and crossed the room toward her. Without thinking, I wrapped my arms around her in a soft, girlish embrace. She didn’t return it right away she just let me melt against her, let me need her. And then, I felt it.

Pressing against my stomach, firm and unmistakable beneath her trousers… a strap-on.
My breath caught. My cheeks flushed instantly, heat rushing to my face. I looked up at her she was already smiling. That slow, knowing smile that said she planned this. Without a word, she cupped the back of my neck, pulled me into a kiss that was deep, full of promise, and just a little bit dangerous. I whimpered softly into her mouth as she pushed her hips forward, grinding the shape of her cock into my thigh. It was deliberate. Possessive.

“I thought you might like this,” she whispered against my lips, her voice low and silky. I nodded, barely able to speak. My body was already reacting trembling, eager, wet.

She stepped back just enough to look at me, her eyes scanning every inch of me like I was hers to inspect… and I was. I am. Standing there, dressed as Steph, I suddenly felt very small next to her

All I could say was, “Thank you, hun.” She smiled wickedly and said, “I want you to feel like a girl on a naughty weekend getaway.” 

She ordered room service a steak for her, and a light salad for me, with a cocktail to match. Even that made me purr. She was caring for Steph, treating her like her own little princess.

Later, as we sipped our tiny wine bottles, from the minibar, my heart swelled. Lipstick stains on the glass, long nails wrapped around the stem, and a handbag packed with all the things a girl could need, tampons, perfume, my phone, a little purse. Lucy had thought of everything.

She doesn't always find it easy. Some days she's confused. Others, she’s supportive and amazing. But no matter what, she still loves me. Even when I feel like less of a man. Even when I feel like I don’t deserve her.

There was a knock at the door, and I scurried (or rather, stumbled in my 5-inch heels) to hide in the bathroom, much to Lucy's laughter. The poor room service guy had no clue. When it was safe, I came back out and we sat down to eat.

We chatted like girlfriends. She asked me so many questions, what I like, what started all this, if I’ve ever been with a man. And for the first time in my life, I was totally, completely honest. Yes, I have. Yes, I do fantasize. Yes, I wish I was prettier. More passable. More girly.

And then she told me a wild story about a holiday in Greece… Let’s just say it involved two men and one very adventurous night. I blushed so hard I thought I might explode. But it made me realize something: so many women are so much more open and experienced than we think.

As the night drew on, she laid out my baby pink babydoll and matching panties and told me to get ready for bed. I was still nervous, she made me put the room service tray outside while dressed. It was late, the corridor was empty, but I swear my heart nearly stopped. I dashed back inside like a cartoon bunny.

Lucy was already undressing. She handed me the babydoll and told me to take off my makeup. I stepped into the bathroom and obeyed her instructions, gently wiping it all away until the cotton pads were stained with pinks and browns. I hung my outfit on the back of the door and placed my lingerie gently on the small shelf full of towels, the lingerie was my prize possision and I sooo wanted to keep it forever. I stepped into the lacy babydoll and matching knickers, slipped on my heels, and stepped back into the room to join lucy as she was slipping on masculin pair of boxer shorts and that strap-on was still there, bulging under the front of her shorts

As I walked towards Lucy tryng my best walk as sultyly as possible, the soft swish of my babydoll brushing my thighs made me shiver with delight. My heels clicked gently on the floor as I walked towards Lucy, who stood tall and powerful in her boxers. Her strap-on peeked through the open fly, and her eyes sparkled with amusement and affection.

Without saying a word, she loosened the bun she had tied my wig into earlier, letting my curls fall gently around my face. Then, with a firm but loving hand, she guided me down to my knees.

The moment was surreal, like I was both inside my body and watching from above. Here I was, nails long and elegant, lips still slightly stained pink, wearing delicate lingerie, kneeling before the woman I adored. I could hardly breathe. She looked down at me and smirked, brushing her thumb across my cheek and whispering, “Good girl.”

What followed was… intense.

Tender, yet commanding. Loving, but laced with a delicious cruelty. There was wickedness in her eyes, but never without love. I felt entirely hers, Steph, not Matt. Not pretending. Not performing. But becoming.

She didn’t just dress me like a woman. She saw me as one. Desired me as one. Claimed me as one.
And in that moment, I came alive.

She guided my hand, gently but firmly, to the opening in her boxer shorts. My fingers trembled slightly as I reached in and found it, her cock. Silicone, sure, but it might as well have been flesh with the way my body responded. I pulled it free, marveling at the smooth weight of it in my hand. My feminized hand. Even in that electric moment, I paused to glance down at my french tipped nails wrapped around her shaft, and I couldn’t help but smile. God, my hands look so pretty.

I looked up at her, Lucy, my wife, my goddess and she nodded once, slowly, like we were crossing a threshold together.

And then I took her cock into my mouth.

The taste was faint, more rubber and scent than flavor, but it didn’t matter. My lips wrapped around it, my tongue swirling instinctively, my whole being focused on pleasing her. I bobbed my head, slowly at first, feeling the way the harness shifted with her hips, the way she gripped the back of my head with one hand, tangled fingers in my wig, and held me exactly where she wanted me.

Her voice cut through the haze, low and vicious and impossibly arousing.
“Suck it, bitch.”

She tugged my hair hard and I whimpered. The humiliation sent a pulse straight between my thighs. I moaned around her cock, the sound muffled but desperate, needy. I loved it. Every degrading, delicious second of it.

Because in that moment, I wasn’t failing her. I wasn’t disappointing or broken. I wasn’t inadequate or ashamed. I was hers. Her girl. Her toy. Her wife.

This wasn’t just play. This was a shift, seismic, irreversible. Our dynamic had changed, deepened. She was still my Lucy, still gentle and nurturing. But now she was also something more a mistress of my desire, a sculptor of my identity. And I, Steph, wanted nothing more than to be shaped by her hands.
I felt something stir in me not just arousal, but peace. Joy. Belonging.

As I worshipped her, as she whispered filthy things that made me wetter than I thought possible, I knew this wasn’t a one-time fantasy. This was us now. And I never wanted to go back.

And when we finally curled into bed, wrapped in the softness of hotel sheets, she pulled me close and whispered, “You’re perfect just like this.” I fell asleep in her arms, feeling more like myself than I ever had in my entire life.

I woke to the gentle hiss of the in-room coffee pod machine coming to life, the sound somehow comforting and grounding after the night I’d just had. My hair, still perfectly tangled in that wild, slept-in way was a glorious, feminine mess. My false lashes were slightly askew, and I was still wrapped in my sheer little babydoll, the fabric cool and delicate against my skin.

Every inch of me ached in that tender, satisfied way that only comes from being thoroughly, lovingly… claimed. I stretched beneath the hotel sheets, my body humming with the sweetest soreness. I could feel the soft give of my breastplate still clinging to my chest, the familiar weight of my silicone curves pressing down into the mattress. Last night hadn’t just been a fantasy come true it had been a transformation. Steph had given herself completely, and for the first time in her life… she was no longer a virgin.

I'd dreamed of it, fantasized about it, written it into journal entries and whispered it into pillows. But nothing could have prepared me for the real thing. For being seen, touched, and loved as the woman I longed to be.

Across the room, Lucy stood by the window in a fluffy hotel robe, her bare legs catching the soft morning light. She was sipping from a dainty white espresso cup and looking out at the city below, calm and confident, as if everything in the world had unfolded exactly the way she’d planned. When she turned to face me, she wore that sleepy, knowing smile the one that says, Yes, baby… that really happened. And I loved every second of it.

Then, without skipping a beat, she smirked and said, “So babe… did you enjoy sliding up and down on my cock?”

I gasped half shocked, half thrilled. Lucy was still in character. My face flushed pink as heat bloomed between my thighs. There was no post-orgasm shame, no awkwardness, no guilt just that electrifying sense of still being Steph, fully, truly, undeniably her.

Lucy sauntered toward the bed and added casually, “Now you see why a girl needs a good seeing-to once in a while.”

I bit my lower lip and nodded, too overwhelmed to speak. I was caught in that sweet, fragile space between raw emotion and sheer exhilaration. I wanted to giggle, but instead, my eyes welled with tears. And before I could stop myself, I blurted out, “I’m so sorry…”

Lucy tilted her head, soft concern flickering in her eyes. “Sorry? For what?”

My voice trembled. “Because I can’t give you sex the way you need it. And you’ve been so kind so amazing to help me live my truth. It feels selfish.”

Her expression melted into something deep and tender as she walked over to me, bent down, and handed me a coffee cup, and kissed my forehead with a loving, sleepy sigh. “Morning, princess,” she whispered with a wink.

And just like that, I melted.

We curled up in bed with our drinks, giggling between sips. She teased me mercilessly about my bedhead and the way I moaned like a pornstar, and I teased her right back about her power suit and strap-on swagger. But beneath all the playful banter, there was something more a quiet intimacy, a sacred bond forged in the dark and sealed in laughter. Something had shifted. Something real.

An hour passed in a dreamy haze. Then came the inevitable packing.

I slipped out of my babydoll, the fabric falling to the floor like a whisper, and began sorting through the little pile of clothes, lingerie, and accessories that had made me feel more like Steph than I’d ever felt before. Lucy joined me, helping me to peel off my silicon breastplate, folding it gently like it was sacred. Then she reached for her micellar water and a handful of soft cotton pads.

“Come here, baby,” she murmured.

I sat in front of her cross-legged on the bed while she delicately wiped away the lingering traces of my makeup. With each stroke of the pad, it felt like she was saying, You were beautiful last night, and you’re beautiful now.

Once I was back in what we jokingly call “Matt-mode”—hoodie, joggers, trainers, and no makeup—I caught sight of myself in the hotel mirror. My reflection looked so ordinary, so neutral. But inside? Steph was still glowing.

Lucy must’ve seen the flicker of sadness cross my face. She came up behind me, wrapped her arms tightly around my waist, and kissed the side of my neck. “She’s still in there,” she whispered. “And she’s not going anywhere.”

Tears welled up again.

I wanted to share this with you Ms Kate in the hope that it might help girls like me. I wish everyone had a Lucy in their lives.


All I can say is Lucy, we adore you. Steph thank you for your email.