Crossroad Moment (A crossdressing story based on true events) (Patreon)

Thank you Bryan for being a top-tier supporter and waiting so patiently for this. I hope you like it:)

Crossroad Moment.

We all know that feeling.

That raging excitement you feel when you’re finally in the house alone. The pulse of energy You feel when you see your sister's clothes just hanging there, only tempting you further.

That surge of adrenaline you get when picking up a single item of female clothing that society says you shouldn’t be wearing as a man. That desire to feel it and see it on your body.

It’s that same desire that hounds you to wear more—to do more and go that extra mile deeper into the rabbit hole. That rabbit hole makes you want to look and feel like a woman.

If you know what I’m talking about, then you’ll likely understand the dilemma I find myself in.

Sitting on the edge of my bed, I look down at the heels beside me and I feel those exact feelings. I’d love to tell you that they are mine, but alas…they are not.

The smooth glossy heels cry out to me to wear them! I want to strut around this room with my feminine attitude, but I know I must not!

They belong to my girlfriend, but I’m getting ahead of myself. To understand my dilemma, I think I must start from the beginning! To be honest, I’d imagine you the reader have had many of the same experiences!

It’s funny I should be talking about wearing my girlfriend's high heels. My mother's high heels triggered the first time I realized I was different from the other boys.

As a young child, I’d often be in the room as my Mother got dressed. Being the youngest child, I was attached to her like glue—desperate for any attention I could get.

I remember vividly the pair of black heels my mother kept in the closet. I’d always see them at the bottom of the closet, unworn and unloved.

“Why don’t you wear those ones, mommy?” I’d ask, pointing at the mysterious-looking shoes.

“They hurt me, baby…,” she’d respond with a wry smile.

That always left me so confused.

I remember thinking that they look so pretty and that they’d surely only make my mother feel good about herself. So how could they hurt her in any way? (Obviously, now I understand what she meant)

For some reason, that question stayed with me. Every time I’d be in the room with her and she had the closet open, those same shoes would call out to me. I had to know their secrets! I had to wear them myself!

That’s exactly what I did!

My mother did a lot of gardening, and I knew this one day she’d be outside for a while. So I told her I wanted to go play in my room for a while. Running up the stairs with my heart beating, I snook into her room and snatched the heels from the closet.

I knew I was being naughty, but I couldn’t resist. I didn’t understand my feelings at the time but, I just knew I had to try them on! I had to know how they felt!

Scurrying into my room, I stood in front of my small mirror with a huge smile on my face. I remember just how big and heavy they felt in my little hands, but that didn’t stop me!

Being careful to stand the heels side by side, I stood into each one still wearing my spiderman socks. As my small toes nestled into the pointed ends of the heels, I stood taller.

Even though I couldn’t walk in them or really move without my feet just coming straight out, I loved every second! Just knowing they weren’t meant for me was so exciting!

I think you understand what I mean and just how I felt at that moment.

I couldn’t wait for my body to grow and for them to fit me for real. That moment came just after my fourteenth birthday!

I snook in and wore them with pride! Even though I wobbled with every step, they fitted me and felt amazing to wear! (I think I ended up wearing them out. By the end of that year, mom threw them away.)

By this time, I’d started to understand that things for me were a little different. As my friends started objectifying the girls in our school year, I could only feel jealous of the outfits they wore.

“Look at those legs!” Tim would say gleefully, staring at Rachel’s legs in that red skirt she wore.

I’d nod and agree, but really I’d be wondering what it was like to wear that red mini-skirt.

Lucky for me, my keen interest in the girls around me lead to me having a bit of a reputation for being a lady's man. It wasn’t that I made out with all the girls in the school, but I had no problem talking to any of them.

I was just so interested in girls and being a girl, that I felt comfortable around them. Unlike my friends who were just typical shy boys.

One girl, Stephany, quickly became my best friend.

Now Stephany wasn’t the typical girl at my school at the time. She was more gothic and alternative than the Britney spears wannabes.

I really liked that about her! I marveled at the unique outfits and looks she came up with. Plus, I was so envious of her long glossy black hair! (It gave me the motivation to grow my own hair long)

It wasn’t strange for me and Steph to hang out at her house after school. So much so that we had to constantly quell the rumors that we were going out!

That couldn’t have been further from the truth. She’d come out as a lesbian to me very early on in our friendship. That revelation made me trust her with my life.

By this time my crossdressing had become a deep secret of mine. I’d started stashing clothes all around my room that I’d wear at every chance I’d get. That trust I had in her was what lead me to share my fem side with her.

Still, even though she was my best friend, I was very nervous to share. I kept putting it off over and over again, telling myself I’d wait for the perfect moment.

After wasting moment after moment through fear of her not accepting me, she ended up giving me the perfect excuse to bring it up with her.

One day after school, she was doing her makeup. Once she was finished, she turned to me with a wide grin.

“Bryan….,” she smirked, holding up a mascara brush. “Can I put makeup on you?”

I’m sure you know my answer. I jumped at the chance!

I sat in front of her vanity mirror with the biggest grin stretched across my face. I didn’t even try and hide my excitement from her, I was just so thrilled a real girl was doing actual makeup on my face!

Every lotion and potion she pulled from her draws, I wanted to know all about it!

Every stroke and prod with a brush, I asked about and gushed at the results.

Stephany was a saint! She answered every question and even gave advice on shades that would suit my complexion and eye color.

Once she was finished and my transformation was complete, I couldn’t hold it back! I looked her straight in the eyes and smiled.

“Stephany,” I said gleefully. “I like wearing girl's clothes! It makes me happy!”

I remember her expression like it was yesterday! Her face lit up and made me feel so warm inside. It only lasted a second before she was making me try on her clothing, but that first moment of being accepted by her was incredible.

I still find it hard to explain now. It was almost like the darkness was pulled back for the first time in my life. (She also gave me my first taste of feminine underwear! So soft!)

I want to tell you that Stephany and I remained best friends forever, but alas… life threw us a screwball and she moved away a year later. Although we weren’t together, I was heart broken.

The first girl to truly accept me for me was gone from my life in the blink of an eye.

Now, you might be wondering why I’m telling you all this. I have a good reason. Now, like the taps being turned to full, allowing the water to gush out, I knew how it felt to look and dress like a girl.

That gender euphoria was something I desired and wanted as much as possible. My male persona was boring and I barely took care of my appearance, but the girl me was the complete opposite!

By the time I’d left school and had a job of my own, I’d started buying up all sorts of feminine garments and outfits.

Still living at home, I was careful not to get caught and had quite an elaborate system for hiding all my panties and dresses.

It was at this crazy time that I brought my first pair of heels, corset, and wig. It wasn’t long after that my female persona was born and she had her first posts on Facebook!

I still remember getting those lovely comments about my outfit and figure from the gurls online! Like those hormone-filled moments with Stephany years ago, I felt euphoric about my body once again.

Not to mention the cheeky comments from men perving on over the pictures I dared to post!

My body confidence was starting to skyrocket. I started to feel like I was actually worth something in life and that I could look actually attractive and sexy to other humans.

However, my overconfidence caused the moment that my family wishes never to speak of.

I’d been told my mom wasn’t coming back from work until late and the rest of my family was out doing stuff. This meant I was alone in the house and free to let my fem side out.

As I’d done at this point many times, I’d shaved all over, done my makeup, put on my wig, and was deciding on what cute outfit to wear.

My plan, post a load of new ‘sexy’ pictures for my Facebook profile.

I think you can see where this is going. Those ‘sexy’ pictures never got taken. What happened was my mom walked in on me wearing only heels, a thong, and a bra.

Let's just say her reaction was less than pleasant. Please understand that recalling her expressions and piercing words would only cause me to shudder and stop writing.

However, I’m sure you’re curious to know what happened.

I shed a tear as started throwing my collection into the trash. I felt my feminine persona and confidence slide back down deep inside.

My heart whined out as my own mother scornfully forced me to help her tear up and throw away everything that I’d brought.

I couldn’t bring myself to even open my Facebook page after that incident. The disappointment on her face still haunts me. I tried my best to make her understand, but she couldn’t see past her stupid ‘traditional’ upbringing!

Depressing….isn’t it?

Well, please don’t worry dear reader. Things did get better after that.

Remember I mentioned my girlfriend? Yeah, we met maybe half a year later at a work party.

She is everything I wished I could be! Long smooth legs, curves, and a stunning rack to boot. My male friends gushed over how lucky I am to have met her.

Her name is Giselle and she’s the light of my life.

We get on like a house on fire! It’s like what I felt for Stephany all those years ago but amplified all the way up to ten. I love her.

I know you’re wondering….have I shared my fem side with her?

Yes, yes I have.

Giselle was a little taken aback at first, but she was accepting and allowed me to start experimenting with my gender once again without the fear that had blighted my heart since my mother caught me.

Times she’d do my makeup. Other times she’d let me borrow her underwear!

Things were good!

But, as they say….what comes up, must come down. How very true I’d find that to be after one particularly awful drunken disagreement with her.

Turns out that my crossdressing makes her a little sad and worried. It makes her feel like I’m going to leave her for a man or transition into something she can’t love.

I want her to see that it doesn’t matter! Love is love, no matter who or what the person is!

Can you now see my dilemma?

What do you do when the love of your life asks you to change? Well….you change. Nothing can be worse than not having her in my life!

I knew what I had to do.

It’s been months since that fight and I’ve swallowed down all my feminine desires to make it work with the love of my life!

We are moving in together next week and that’s why I sit in my childhood bedroom alone, surrounded by her clothing that’s strewn around the place.

Those heels I spoke of earlier, they are like my mother's before, stuffed into the closet calling out to that part of me!

Should I allow myself to feel good to feel more me by putting them on?

Should I risk the best thing that’s ever happened to me by giving into those felting moments of gender euphoria?

Or should I swallow down the feelings deep and push them to the deepest parts of my subconscious—trapping them away for good so I can live a normal life?

My life is at a crossroads and my head and heart are split!

Should I or should I not slip on those sexy little heels!?

I’m sure just slipping them on for a moment won't hurt.