Exploring Anal Sex and Sexual Identity: A Crossdresser’s Journey

Feeling thrilled and want to take your crossdressing journey to another level? But you’re completely baffled? Well, I understand the feeling because I’ve been there before. Exploring anal sex and sexual identity is not that easy. I’m sharing my crossdresser sex stories and tips to help you work it out.

Crossdressing is all about getting connected to your female side. The journey gets more interesting when you explore your sexuality. Anal sex is all it takes to fully transition. It’s pleasurable, but it’s a learning process. It gets easy with time.

My experience with anal sex is not bad at all. I enjoy every bit of it. At first, it felt a little discomforting. But became more pleasurable as I learned to let it loose. If I did it, so can you!

But again, exploring anal sex can be intimidating. Relax; let me teach you how to deal with all the emotions that come with it. So, let’s get right into it!

The Shift in Sexual Identity: The Emotional Journey

Background

I first came out as a crossdresser when I was 18 years old. But I’ve been crossdressing behind closed doors since I was 14 years old.

I could try on my sister’s clothes and take snaps in our basement. I felt cute, and I got to go outside every Halloween and get fancied.

It was not something I couldn’t do often because of my parents. But each day, I felt like I was not being true to myself.

But college was the beginning of my crossdressing journey. It was also the start of all the crossdresser sex stories I will live to tell.

I met my wife in college, and while we were dating, I opened up about my crossdressing, and she was okay with it. But, I never opened up about my sexual encounters.

My marriage has been good. Each anniversary, my wife and I do roleplay, during which I get to crossdress, and I appreciate it.

But at this point, I have not opened up to her fully yet.

Exploration of Guilt and Self-Realization

When you take it to a new level, it typically becomes complicated. The guilt conscience that comes with exploring anal sex and sexual identity is just real.

Especially if you’re married, we can’t ignore how societal standards pressure us. For instance, I have a lot of crossdresser sex stories to tell my wife. But I feel guilty.

Feeling guilty is normal. You cannot avoid it, but you can actually suppress those feelings. It’s all about self-awareness and empowerment.

Just acknowledge these feelings and treat yourself with compassion. Seek validation from safe spaces.

You can join an online crossdressing community; just go to a gay club and just let it loose.

The Encounter with a Man at the Gay Club

Well, my crossdressing sex stories start here. I was in my final year of college. And had just turned 22.

It was on New Year’s Eve, and my girlfriend (now wife) had traveled to spend time with her parents. After too many glasses of wine, I was getting really curious and horny.

The wild thoughts were intense, and I thought to myself, “What if I get dressed and walk to a gay club?” I couldn’t resist. I just did it!

Fully transformed, I was in a tight, glittering black dress, full makeup, and in my girlfriend’s red bottoms. I walked to this club and went straight to the counter.

There was this gay man from a distance. He seemed so invested in my looks.

He made me feel so sexy that I walked straight to him.

We talked for a while, and sooner or later, we were dancing and grinding on each other. It was getting hot, I led him on, and he walked me to his car.

We were kissing and rubbing each other. Suddenly, he lifted my dress and pinned me on the back seat, and all I can remember is that he was already inside me!

Before I could fully snap back, I realized I just had sex! I cannot deny how guilty I felt afterward. But I can assure you how fulfilling the experience was.

It awoke my sexual side I had not experienced before.

Impact on the Narrator’s Life

Sexual exploration comes with many benefits. It gives you a chance to develop your sexual identity and facilitates good mental health.

It is when you explore your sexuality without shame and fear of judgment that you feel fulfilled. Remain true to yourself even when the odds are against you.

Speaking from experience, I can’t say I hate being bisexual. But I hate the problems it brings to my personal life.

As I write this, I don’t regret having lived to create a series of crossdresser sex stories. But my wife is my real concern. I came out to her today!

She just stormed out without any word. I don’t know how this will unfold. I understand this might be hard on her, so I’m giving her some space.

But I feel liberated!

From Pain to Pleasure: Rebuilding the Sexual Experience

Background

I was once only a straight crossdresser, I can’t really tell how I got here.

Are you just realizing that you’re attracted to men? Perhaps your bisexuality has stayed dormant until recently. Well, welcome to my club!

Rest assured, the feeling is worth exploring. My first anal sex felt so validating. It’s like I was really waiting for that day.

It felt like I was releasing my suppressed emotions and letting go.

Understanding Anal Sex as a New Experience

Anal sex is a unique type of feminine transitioning for a crossdresser. It marks the beginning of crossdresser sex stories you’ll treasure forever.

Moving to the bottom, just from being a straight guy, is a lot of new experience. It feels validating and gives you some emotional satisfaction you’ve never felt before.

The Process of Learning to Enjoy Anal Sex

My anal sex experience has really progressed. It got from a point where I felt uncomfortable to feeling intense pleasure.

It went from feeling discomfort to feeling pleasure. The trick is being presently there. That is, training your mind to focus on emotional and energetic release.

The Importance of Submission and Surrender

Want to make your crossdresser sex stories enticing? Well, you have to submit. Like getting into all that feminine energy.

The hack is to let go and let loose. Don’t be so uptight. Allow yourself to be vulnerable to the sensations. This will make the experience enjoyable and help your body adjust.

Practical Tips for Crossdressers Exploring Anal Sex

Taking It Slow

Exploring anal sex is a step-by-step thing. You have to ease into the experience. Make a slow and very gentle approach to avoid being injured and make it more pleasurable.

Communication with Partners

All your crossdresser sex stories should be from a consensual experience. Set your boundaries and communicate with your partner.

The goal is to make sure that all your sexual needs are met. The moment you feel like the boundaries are pushed, step back. Just take it slow.

Use of Lubrication

Lubrication during anal sex is very important. It has a big role to play when it comes to reducing friction, less discomfort, and making anal sex more pleasurable.

More so, when using condoms, it is unlikely that they will fall off or break.

Preparation and Cleaning

The first order of the day is to clean it pretty well. It’s just necessary! You can douche with an enema for better cleaning. Then shower for outer part cleaning.

Experimenting with Toys

Butt plugs will make your crossdresser sex stories even more interesting. By butt plugs, I mean sex toys.

Sex toys will help you self-explore and actually prepare you for real sex, by allowing you to get used to the sensation and for easier penetration.

Managing Discomfort

It goes back to normal in due time. It depends on how prepared and deep you were penetrated. But the fissures will go away in a few days.

You can first take a break from it to speed healing up. But always run a warm, salty bath after bottoming to bliss it off.

The Emotional and Energetic Dimensions of Anal Sex

Embracing Sexual Vulnerability

Submission is what will elevate your anal sex experiences. For me, surrendering it all helps me to connect while listening to my body.

Energetic Pleasure

Letting go of control during anal sex usually makes it a far-stretched and pleasurable sensation. Once your body and mind connect, you release the emotions, helping you to let go.

The Impact of Submission on Sexual Fulfillment

Letting loose is all that it takes to keep your crossdresser sex stories positive. Submission allows you to experience deeper connections with your partner and validates your emotions.

Conclusion

Crossdressing allows you to experience your feminine side. And exploring anal sex and your sexual identity makes the transition complete.

That’s because you get to submit and surrender most of your sexual control. Once you master the art of giving, regular sex will never feel enough.

The exciting thing about moving to the bottom is that you get to create crossdressing sex stories for a lifetime. You get a chance to live a fulfilling life.

Life is only lived once. So, be yourself and take control of your life. Do what makes you happy, and don’t let societal standards define who you truly are.

Make your crossdressing journey worth it!