There were times when I never thought this day would come, but I think it’s finally time to part ways with my longtime lover, Jey.
I met Jey when I was just 21 years old. Funny enough, our first encounter happened almost by accident. For some strange reason, when he reached out to me on Craigslist, I was under the impression that he was a Black man (my favorite, lol). But when I arrived at his apartment, I was completely caught off guard. Standing in front of me was a Sri Lankan man, someone I never imagined I’d be attracted to.
I’ll admit, I almost turned around and left. I just wasn’t interested. But then he did something that no man had ever really done for me before. He treated me like an actual human being.
Not just some crossdresser who was there to suck his dick and leave, but an actual person. He was polite, sweet, welcoming, and even offered me a drink. Something about the way he treated me made me want to give him a chance.
And I’m so glad I did.
That one unexpected encounter turned into an incredible 15-year relationship.
Jey has played such a significant role in my journey as a crossdresser and sissy. He was fun, passionate, intense, respectful, and, most importantly, accepting of me in every form.
When we first started seeing each other, I was a very basic crossdresser. I wouldn’t even shave my goatee because I was terrified of someone finding out about my feminine side, lol. But Jey didn’t care. He was perfectly happy seeing me in my little dresses and cheap wigs.
In those early days, I was also hesitant about taking things further sexually. I wasn’t ready for anal sex, and although I’m sure he wanted it, he never pressured me or made me feel bad about it. He respected my boundaries. Instead, we shared plenty of passionate kissing, touching, and oral sex. I loved pleasing him, and he always made me feel wanted.
As our relationship grew, so did my confidence, my curiosity, and my understanding of crossdressing. And Jey got to experience that transformation firsthand.
There was always something so exciting about preparing to see him in a new way. I still remember the first time I completely shaved my face and body for him. Feeling that silky-smooth skin and seeing how much he loved it was such an incredible experience.
Then came the first time I really splurged on a beautiful outfit, a nice pair of heels, and a proper wig. I remember how feminine I felt, especially when he complimented me and couldn’t seem to keep his hands off me. Those moments did so much for my confidence. He made me feel beautiful, feminine, and sexually desirable.
And, of course, there was the night I finally felt comfortable enough to have anal sex with him. Wow, what an intense and unforgettable experience that was!
Looking back, I can’t help but smile at how much I changed over the years. I went from being incredibly reserved and nervous about anal sex, struggling through those first few uncomfortable experiences, to eventually becoming someone who genuinely enjoyed it and confidently expressed what I wanted in bed. It’s almost funny thinking about how shy and hesitant I once was compared to how sexually open I eventually became with him.
Over time, Jey got to witness so many different versions of me. From the shy crossdresser hiding behind a goatee and a cheap wig to someone who became comfortable wearing makeup, dressing more femininely, and even walking outside fully dressed on my way to see him.
Our sexual relationship evolved right alongside my confidence. Jey introduced me to poppers, and experimenting with them became another part of our intimate experiences. Looking back, it’s remarkable how many new things we experienced over those 15 years and how comfortable I became sharing my desires and curiosities with him.
And it wasn’t just the moments we spent together that made our relationship special. Even when we were apart, Jey was constantly on my mind. I can’t tell you how many times I found myself masturbating while thinking about him. For years, the majority of my fantasies revolved around Jey. I’d imagine seeing him again, feeling his hands against my skin, remembering his kisses, and reliving those intimate moments when he made me feel so desired. Sometimes it wasn’t even about the sex itself. It was the anticipation of being with him, the excitement of dressing up for him, and knowing how much he wanted me.
He became such a central part of my sexual identity that, for the longest time, I could hardly imagine my intimate life without him.
And through all those changes, he continued to accept me.
But as much as I cherish everything we’ve shared, time has a way of changing things.
When Jey and I first met, I was only 21, and he was somewhere in his mid-to-late 30s. Fifteen years later, I’m still relatively young, in my 30s, while he’s now in his 50s. Naturally, we’ve both changed over the years, especially when it comes to our sex drives.
Over the last couple of years, I’ve noticed his sexual stamina and desire aren’t quite what they used to be. Don’t get me wrong, we still have fun, and there are moments when that old passion comes rushing back. But getting to those moments has become increasingly difficult.
Jey can still happily lie back and enjoy receiving oral sex for as long as I’m willing to give it, lol. But when it comes to anal sex, things have become much more challenging. He struggles with erectile dysfunction, and it often takes multiple attempts before we’re able to have the kind of sex we once enjoyed so effortlessly. Even then, those moments can be brief, interrupted by long pauses, kissing, and attempts to regain the momentum.
And while I absolutely love kissing him, sometimes I find myself wanting more.
The irony is that after all these years, just as I’ve finally become confident enough to fully embrace and enjoy anal sex, it’s become something he can no longer consistently give me.
I want passion, stamina, and consistency. I want to experience intimacy without constantly worrying about whether things will work out physically. I want to explore the sexual confidence I’ve spent so many years developing.
And I realize that those desires don’t make Jey any less of a man or diminish what we’ve shared. He’s getting older, and his body is changing. That’s simply part of life. I don’t resent him for it, and I certainly don’t want him to feel inadequate because of something he can’t always control.
But I also can’t ignore the fact that my own desires are moving in a different direction.
In some ways, I feel like I’m entering an entirely new chapter of my life as a crossdresser. I’m more confident, more comfortable with my femininity, and more aware of what I want sexually than I’ve ever been.
And I want to experience that while I still can.
I know I’m not going to be young forever. Eventually, my body will change, my skin will age, and perhaps my own sex drive will slow down. That’s a reality we all face. But right now, I’m still in my 30s, I still have a strong sexual appetite, and I feel like there’s an entire world of experiences I haven’t allowed myself to explore.
One fantasy in particular has stayed with me for as long as I can remember: being with a big, muscular Black man.
It’s always been one of my biggest sexual desires. The physical attraction, the masculinity, and the thought of finally exploring something I’ve fantasized about for so many years have always excited me.
And yet, despite how badly I’ve wanted that experience, I’ve always hesitated.
Part of it has been intimidation. I’ve sometimes worried about being with someone who’s physically bigger or more sexually demanding than I’m accustomed to. But I think the bigger reason has always been Jey.
With Jey, I knew exactly what to expect. I knew his body, his personality, his touch, and the way he made me feel. I never had to worry about being judged or rejected for being a crossdresser. I could simply be myself.
That kind of comfort and acceptance is incredibly difficult to walk away from, especially when you’ve spent 15 years building it with someone.
But lately, I’ve started wondering whether that same comfort has also been the very thing keeping me from exploring the experiences I’ve always wanted.
And perhaps that’s the hardest realization of all. Jey hasn’t done anything wrong. He hasn’t stopped being the sweet, accepting man I met all those years ago. Our relationship hasn’t ended because of some terrible argument, betrayal, or resentment.
We’ve simply reached a point in our lives where what we want, and what we’re able to give each other, no longer quite aligns.
I’ve spent a lot of time thinking about this, and I’ve realized that as wonderful as our memories are, lately that’s what I’ve been holding on to: memories. The last handful of times we’ve been together have shown me what our relationship has become, and I don’t think it’s what I want anymore.
That doesn’t mean saying goodbye will be easy.
I’ll miss more than just the sex. I’ll miss his kisses, his affection, falling asleep beside him, and those quiet moments when I felt like his girlfriend. There was something incredibly special about lying in his arms, knowing that for those few hours I could simply be Aubrey. I wasn’t pretending or hiding. I was his girl, and he wanted me there.
That’s something I hope to experience again someday.
I want to meet someone who knows I’m a crossdresser but still sees me as beautiful and treats me like his girlfriend. Someone who finds me attractive, enjoys my femininity, and genuinely wants to spend time with me. Someone I can exchange sweet messages with, look forward to seeing, spend a weekend away with, and fall asleep beside.
I don’t want to rush into random hookups. I want chemistry, affection, excitement, and hopefully another meaningful connection. I want to feel wanted, not just sexually, but as a person.
And I’m excited about continuing to grow as Aubrey. I want to keep getting in shape, improving my makeup, finding outfits that flatter my curves, and building the confidence to finally step out into the world dressed femininely. Maybe someday I’ll experience that first public outing with someone who makes me feel safe, beautiful, and proud to be seen.
I don’t know when I’ll meet that person, or even if I will. Maybe I’ll spend some time simply enjoying crossdressing on my own. And honestly, I think I could be happy with that too.
I haven’t told Jey goodbye yet. That’s probably the hardest part still ahead of me. I’m nervous about hurting him, and I’m nervous that if he asks me to stay, a part of me will want to. After 15 years, it’s difficult to imagine closing that door.
But I think I’m finally ready.
Jey will always hold a special place in my heart. He helped me discover, embrace, and love a side of myself that I once felt I needed to hide. Nothing that happens next will ever take those memories away.
I’ll always be grateful for the young crossdresser he welcomed into his apartment 15 years ago, and for the woman he helped me feel like along the way.
Maybe the most bittersweet part of saying goodbye is realizing that someone can mean so much to you, and you can still be ready for a different future.
Thank you for everything, Jey. ❤️