"Good night!" I said to the last few coworkers who were in my desk area. The short walk out to my car was freeing, as I knew I had about a 45 minute ride home to blast some tunes and decompress. I had just recently turned 30 and got engaged to my long time girlfriend within the last 2 weeks (mostly due to the pressure I was receiving from friends and family). Lots of life changes were happening at once and I was feeling overwhelmed almost daily. My car rides home to our apartment after work became a time for me to unwind alone and just be myself. "Hey Siri, play Dua Lipa". As I flew out of the parking lot, rolled my windows down, and cranked my volume to the max, my stresses started to fade.
I had been together with my girlfriend for close to 10 years. We were friends in college, and midway through our Senior year after a party one night (and a little too much tequila) one thing led to another, and we hooked up. The next few weeks led to a few more hookups, which snowballed into a relationship. I had never had a girlfriend (or been anywhere past second base) with a girl prior to this, so it was all pretty exciting. We have always had a unique and close relationship, but what she doesn't know to this day is that over the years I have struggled, and continue to struggle, with my sexuality. After we started dating I was able to suppress my feelings and enjoy a relatively frequent sex life, which has lessened (both in frequency and the strength in my erections) over the years.
I have never gone far enough to actually experiment sexually with another man. As I've continued down the endless rabbit hole of now widely and easily accessible porn over the years, I eventually found myself almost exclusively watching sissy, CD, and trans content. What also changed over time was my view towards the content itself- I started to picture myself as the 'girls' in these videos instead of the men. Their smooth feminine bodies, sultry makeup, slutty lingerie, heels, nails, wigs, chastity cages, all meticulously premeditated with the intention of presenting themselves to a dominant man for their pleasure- I was infatuated. I found myself completely taken by these fantasies of being used by a real man; being broken and forced to accept my role as a beta by a strong, dominant alpha male.
Sissy Hypnos became my everyday go-to. Seeing these gurls, once boys like me, willingly and happily give up their masculinity and fully embrace the role of the submissive bottom was exhilarating. Over time I also developed a particular infatuation with interracial sissy porn. Not so much the "BNWO" culture, which is frankly over the top and out of touch with reality, but something about the black male form, to me, is perfection. The contrast of skin color, a giant dark black cock inside a cute pink bussy- it turned me on like none other.
My 20's, while most boys were out partying and chasing girls, were spent experimenting with makeup, trying on lingerie, and finding whatever suitable household object I could to use on my ass. What helped to reinforce my fantasies was the fact that I'd always had more feminine qualities than masculine. I've always been on the slimmer side but have wide set hips and a naturally plump butt. I had never been much for the gym, so my figure was soft in appearance and I barely had any muscle on me, but was not fatty. I've never been able to grow a beard, have almost no hair on my chest, ass, arms, or legs, and have natural, pouty lips. My blonde hair is super straight, so I've always found it easier to keep it a bit longer, around shoulder length. But most of all was my penis- a measly 1 inch when soft, and 5 inches hard on a good day. Even if I wanted to be just like any other guy, my genetics had seemingly sealed my fate and my role as a sissy.
Despite all this, I had somehow managed to keep my urges to myself up until this point. Throughout the years, I've revisited my sissy side on occasion when I have the urge and the opportunity. Most times I knew I would have the apartment to myself for a couple days, I would load up my Amazon cart and treat myself to a nice wig, some matte lipstick, lingerie sets, stockings, butt plugs, dildos, lube, clip-on earrings, false lashes, and all kinds of girly accessories.
Those 2 or 3 days would consist of hours upon hours of playing dress up, sucking, and fucking myself into ecstasy. I would chat with guys on Reddit and Grindr, only to exchange pics, talk about all the slutty things I'd like to do with them, but ultimately back out of meeting. Multiple orgasms lead to PNC, guilt, and resentment towards not being able to live this way all the time, which lead to me throwing away all my fun toys after every session, and going on with "normal" straight life. This kept the urges at bay- up until I met him...
As I was nearing my apartment, my mind started to wander, as it usually does, to what it would be like. What it would feel like to finally meet a big, strong, masculine black man and experience true pleasure in his arms. To give myself to this man and allow myself to become the object of his desire, to have him call me names like "good girl" "sissy" and "slut", and for me to call him "Daddy" or "Sir". And as per usual, I told myself that it would never be; just a fantasy..
Just as I was yet again preparing myself to park in the lot across the street, shut off my thoughts, and walk over to my building, there he was. 6'5, dark toned, handsome, absolutely ripped. He had strong features, his hair buzzed short with a full but neat and well groomed beard. My eyes raced over him, darting over his muscle tee and shorts, which were lightly gripping his thighs and obvious bulge. He was carrying a yoga mat, a small black bag, and a water bottle. The unmistakable bulge in his shorts (which looked huge!) dropped my mouth open and I had to snap myself out of my trance that this God of a man had suddenly put me in. I put my car in park, grabbed my backpack, and shut the door. He was walking away from my building towards me, to what I assumed was the yoga studio down the road.
Did he live in my building? Had he noticed me before? Is he single? I wonder how big his cock- shit, snap out of it!
Just as we were about to pass one another, I glanced up at him, we locked eyes, and with a slight head nod he casually said "What's up?" OMG- be cool be cool, what should I say back?
