January 2023

By  Jacklyn Henry

 

Alexander’s lips feel heavy on my skin, as he kisses my neck, as he moves down slowly, unbuttoning my shirt, then my pants. We had met a few hours earlier, at a street café in a gentrified part of town, on a street when one could score low-grade heroin without any trouble only a few years back, a street where everything changed when big money showed up, bought all the boarded-up buildings and converted them to hip, trendy condos. 

Unlike the majority of my young millennial neighbors, I had lived on that street since coming to California straight out of college in 1991, having landed a job with a prestigious and somewhat bellicose law firm run by older straight men with bad combovers and poor clothing choices. Eventually I bought the building from the city, a four-story office building destined to be converted into lofts, kitschy art, and variety of LGBTIA creatives.  

“May I?” Alexander looks up at me with big round blue eyes filled with hope and anticipation, his hands prepped to pull my 505 jeans free of my body. 

“Of course, love,” I purr as I dramatically throw my head back, eyes closed, mouth slightly ajar, lipstick perfect as always, and sigh with an extended exhalation. 

It takes but a minute for the younger man to pull me free of my designer skinny jeans. He leaves the black hip hugger panties in place, but exposes my cock for his waiting mouth.   

“My God,” I mutter. Alexander says nothing, as his head bobs up and down. I pull my legs back and offer him my pussy, my asshole, and he quickly redirects his attention. As his tongue pushes into my anus, I place both hands on his head and pull him forward, begging his tongue deeper into my orifice, my pleasure center. 

Voices of merrymakers and drunkards drift up from the street café where Alexander and I had met. The Golden Pickle served expensive drinks to the tourists and reasonably price beverages to locals, especially tenants of the building. And on the house for the owner, which would be me. It would be another few hours before night found its quiet and lovers returned to their hiding places to engage in vigorous coitus with people they barely knew.  

Over the preceding couple of years, the building, as well as the surrounding neighborhood, had grown increasingly queer, which drew the attention of the curious and the adventurous. Some were trolls seeking out a quick fuck or a box to check off or to fulfill some random obsession mainstream society would never understand. Taking it up the ass or sucking cock, or seducing a transgender woman. Getting fucked by a stranger came with my territory, my world view. Some of the other girls, and fellas, to a lesser degree, had standards I didn’t even understand. Apparently, my standards were well below the standard. Whatever. A girl has needs.  And this bitch has plenty.   

Alexander rolls me on to my stomach, my ass fully exposed. I feel his blood engorged penis rub between my ass cheeks. The luscious feeling of vulnerability envelops me, as I impatiently await his entry.  

“Raw?” Alexander whispers shyly. 

“Your call.”  

I listen as Alexander anoints his erection with lubricant, then does the same to my eager pussy. He slips his index finger to its hilt, and I gasp audibly, embarrassing myself only slightly. He quickly pushes in a second finger, grazing my prostate. Precum oozes from my sissy cock. 

Alexander worked at a bank downtown, doing something he could not clearly explain. A few years back he graduated from a nameless school in a small town in a flyover state somewhere in the middle of nowhere. I couldn’t stop staring into his eyes as he shared his origin story. A little over six feet tall, muscular, thick arms, big hands, 100% masculine, I immediately wanted him.  

I could sense Alexander’s desire immediately. His eyes undressed me. I bathed in his attention, gloriously. 

“You are so pretty,” he had said and I laughed. 

“That’s sweet.” 

“No,” he slammed back the last of his first drink, “I think you are.” 

“Well,” I leaned into him, “as long as you do.”  

His penis feels enormous as he presses it into me with a mix of urgency and gentleness. I pull my legs back further as he leans forward to kiss me. Once he pushes the length of his cock completely in, he pulls slowly back, just about halfway before thrusting forcefully back. He repeats the motion, increasing his tempo with each thrust, until he finds his rhythm. 

“My God,” he moans. 

Indeed.

Alexander mentioned a boyfriend that he had recently broken up with over alleged cheating, by both men. He had found a safe place at the café and with each drink, his opened up more. I didn’t have to ask much, it just spilled out of him. 

“What about you?” Alexander asked finally. 

“Ask away, honey.” 

Alexander sat back in his chair, sipped at his fifth drink, and thought a moment. 

“When did you start your transition?” He asked the question quietly, as if the bar staff and most of the nearby regulars didn’t know, or couldn’t tell. While I never went so far as to wear a dress or skirt, or even a true female blouse, I dressed with a degree of femininity that would leave no question as to my orientation.  

“I didn’t.” I laughed. Certain types of people inquired about my sexuality on a fairly frequent basis. Cops, Doctors, Lawyers, random straight people on city streets at any given moment in the day. I just smiled, said nothing. Nowadays people are just absolutely obsessed with labels. When pushed I use ‘queer.’  

After fifteen minutes Alexander cums deep in me, frozen in place until the spasms of pleasure finally stop. 

“Thanks,” he mutters as he quickly retreats, gathering his clothes and dressing.  

I sigh as I lock the door. 

After a quick shower I pull on fresh panties, booty shorts, and an oversized sweater. I fold into a couch and stare out a window as the voices of merrymakers and hipsters drift up from the street. 

My cellphone vibrates to life and a message from a past lover asks to come over. I respond that I am not available and turn my phone off, just as tears silently fall from my eyes. 

© jacklyn henry 2022