How Wearing Boy Shorts Intensified My Kink and Sexual Confidence

As a man, I found a way to harness both feminine and masculine energy

Ana stood nervously across the room until I told her to kneel, place her hands in her lap and look at the floor. Our relationship was her foray into BDSM and being in a submissive role. The dynamic captivated her.

She followed my directive and then I told her to wait as I walked into the bathroom clutching a small bag. I had a surprise for her and felt like I was taking a chance, but so be it. The risk was exciting, likely because I wasn’t sure how it was going to turn out.

I walked in, slipped out of my jeans and underwear and pulled out the boy shorts that I bought in the lingerie section of the local department store. They fit so nicely — tight, yet the fabric was quite comfortable and soothing. A frilly pattern sewn around the edges, making them extra cute.

The feminine energy that came over me while wearing them was one of power and strength. I felt like I was able to capture the femininity that has long flowed through my sexuality, while maintaining my role as the sexually dominant one in my relationship with Ana.

I stepped back out and stood with my legs shoulder width. My cock was hard, outlined by the fabric.

“Look up,” I said.

Ana gasped as a look of desire swept over her.

I had known her for a couple of months and she enjoyed my interest in BDSM. That was a part of me that she found attractive. We hadn’t taken discussions too far so she didn’t know about my interest in women’s panties.

Women’s lingerie plus thongs and bikini bottoms have always fascinated me. There’s an allure about the silkiness and flowing material that enhances a woman’s physicality — the roundness of breasts, hips and ass. For so long, I had wanted to capture the inner essence of that physical beauty and now was the time to do so.

Ana crawled to me when I told her, slowly as I directed, and when she reached me I could tell she was hungry for my cock, erect and throbbing. At this moment, I imagined myself more like a dominant woman, a domme, than I did a dominant man.

I let her slowly lick up my legs and inside my thighs before slowly pulling off the boy shorts and taking my erection in her mouth.

Lingerie first caught my interest when I thumbed through the small glossy ads in the back of my mother’s Cosmopolitan magazines. I’d scan the pages when she was out and later, when I had a maximum amount of privacy, I discovered her lingerie drawer. The fabrics stimulated me like catnip does a feline.

Trying on her teddy and lacy nightgowns gave me a sense of beauty and lightheartedness. I’d lie on my bed, reveling in the sensation while masturbating and considering this form of bliss and longing for another world.

Those experimental times were few and cross-dressing itself never became a regular occurrence for me. I admired a woman’s physique but never felt I could achieve the standard that I longed for.

As an adult, panties held more of a fascination and lingerie less so. The curve in the design around the hips makes my heart skip and fuels me with a slight rush. There were a few times that I’d buy a pair and take them home, feeling like I was a double-agent sneaking secrets from enemy territory.

The more feminine panties and thongs I tried on but they didn’t fit well around my cock. Images of men wearing thongs or bikini briefs didn’t arouse me.

Boy shorts, however, were the perfect answer to channeling both feminine and masculine energy. They fit well, like a pair of tight-fitting running shorts. Lacy edges made me feel pretty while fitting my body and doing justice to my cock.

Ana said later that when she saw me in them she nearly had an orgasm from the visual surprise. Wearing them gave me a sense of power and kinky confidence — a sexual confluence that brought my masculinity into alignment with my feminine interests.

The last time I wore boy shorts was as a submissive to a domme who enjoyed her subs in women’s panties. I modeled for her and in the context I felt far more submissively feminine than I did powerful or masculine. My emphasis mentally was more on the lacy fabric and prettiness versus feelings of possible strength.

Wearing boy shorts for her motivated me to work out and be in shape, pointing out to me the subtle difference between a man and a woman’s attractiveness. For women, we celebrate the curves and areas of softness while for a man we admire the flatness of his abs and the strength of a muscular ass.

Boy shorts, I’ve realized, can fit either sex and seem closely related to the trim feeling of today’s tightly sewn sports briefs for men.

How many men really enjoy wearing them or at least fantasize about them? Who knows? There’s certainly not a one-size fits all answer as noted in this question via a health site, Go Ask Alice, sponsored by Columbia University. A woman says her boyfriend likes to wear women’s underwear because of “how to feels” and asks if that’s “normal.”

The answer is that men have personal preferences and enjoying a physical sensation can be a valid reason for a man to wear women’s panties.

I’ve not worn boy shorts for some time and whether I will again or not, I don’t know. I must say I’m self-conscious and, maybe this is how women feel, I want to be in my best possible shape if I slip them on.

Certainly, I’ll always admire the cut and style on a woman and I believe I can appreciate them on a man as well.

Boy shorts reveal how fashion has evolved to enhance our physical bodies and accommodate our views of personal sexuality.