Strapped
There was a constant frenzy in San Francisco in 1999, months before the infamous Y2K. People were stockpiling water and food, worried about a mass computer crash. The perfect backdrop for a city that continued a class divide between the haves and have-nots. Tech, or the .com industry as it was referred to, was booming, and the aughts first "Tech bros" were emerging. JFK Junior clones in their Patagonia vests over crisp white button-ups, denim, and loafers scattered the streets and littered my Mission St. bars.
The animosity from my tribe—the tattoo artists, waiters, bartenders, artists, and creatives, the "have-nots,” loathed the invasion. Weekend warriors crept over from Noe Valley, Pacific Heights, and the Presidio, slumming it in my dingy dive bars for a dirtbag experience. They came to suck our culture like foam off the top of their New Castle on tap. We despised them.
By 10 PM on a Saturday night, the strip club I worked at for extra cash while in art school was already infested with these Patagonia tech jocks. Entitled, arrogant assholes bathing in privilege and normalcy like it was an inherited crown. A non-yuppie man came to my stage to watch me dance that night. He had short hair, a baseball cap, and a strong jawline. As I drew closer, I could tell that despite the masculine presentation and clothes, I was mistaken. She probably passed most of the time, even outside a seedy strip club's dim, smoky lights.
I drew closer to her on the stage, giving her all the attention and ignoring the rest of the hungry-eyed Patagonia’s. On all fours, I leaned into her seated body over the stage, breasts dangling, and let my long hair tickle her neck and face. She smelled ripe, earthy, yet clean and fresh like she had just showered with Irish Spring. Her posture was tall and confident, with a relaxed laissez-faire, boyish slump in the chair. She slipped me a crisp $20 folded in half in my thong as I collected my tips, making it known she wanted attention.
When I got off stage, I asked if she wanted a private dance with me, and she nodded in agreement. We entered the booth, which consisted of a bench covered in pleather for spills and 'liquids.' A red velvet curtain that never fully closed flush to the wall was the only privacy between us and the rest of the club patrons and bouncers. I waited for the song to start and began my seduction sequence.
$60 was my price for a topless dance. I would dance in front of my client with gentle grazes of my breasts on their face and body, pulling away right as their mouth neared a nipple or a hand tried to brush my ass. Like a snake twisting and curving in the sun to escape a predator, I squirmed in rhythm with the music, in perfect rotation to be touched enough to tease, yet not really touched at all. Near the middle of song number 1, I would slip my panties to the side for a peek and say the dance could be upgraded to $100 for full nude, at which point I would slide my knee in between their legs, gently rubbing their hard-on. The easiest next $40.
Payment was to be made upfront, and by the time they stopped to get the cash out, the song was nearly over. Light touching and teasing ensued, and I wouldn't start grinding on their hard-on until the last 30 seconds. All songs were clipped to 2 minutes and 22 seconds, and I began to memorize each song in the library and when they would end. A particular verse or break would click a timestamp in my brain, I knew it was time to ramp up the grinding to request song number 2, 3, or 4.
The second nude song was an additional $100. $200 total. This was usually where it stopped when they realized there was no finale, and they just spent $200 on a 4-minute and 44-second tease. I would tabulate - with 4 more men buying two $100 songs each, I could make $800 more. Or with 8 more men buying only one $100 nude song, I could get to my $1000 goal by midnight. Then, I could go home to pay rent and bills, and only dance one day that week. I liked to do this mental tally during dances. Accounting, list-making, and other mentally rhythmic tasks staved off boredom and distracted me until the finish line. I remained detached, in control, and often bored while I gave lap dances, but no one would ever know it. I am a talented actress.
~~~
Top off, bottoms off, second song. I placed her hands on my breasts and spun around to show her my ass and pussy. When I sat on her lap, I felt a surprise. Something firm and solid was protruding down her leg. A strap-on. She wasn't just a butch-presenting lesbian; she wanted to be treated like a man.
I spent quite a few nights a week at dyke bars in the Castro and Mission; they always let me drink underage with no ID. I was often confused for a lipstick lesbian and went home with women regularly. They were very persuasive when I was horny after a few drinks and they offered to eat me out. I didn't enjoy reciprocating as much. But when they wore motorcycle jackets and wife beaters with their tits taped down and came onto me like a man, though I considered myself straight, I was into it. It was the masculine energy I craved, even if it was from a woman. Confidence to the point of arrogance and eye contact that could devour me. It turned me into the softer woman that I wanted to be.
I had never been with anyone so masc before, and I was fascinated by the strap-on and her desire to play the part of a man in a strip club. Did she wear the dick every day? Or was she just trying this out? I got on my knees in front of her and began to rub my tits on her rubber cock over her pants, acknowledging it and removing any display of surprise from my face. Not a word was spoken while I started to undo her belt buckle and pull her pants down, exposing her tight navy briefs and the secret lump beneath them. Jumpy with excitement, her hands fumbled to adjust and reveal her giant flesh-toned polyurethane dick. She gripped it proudly like a magical sword she had unearthed from stone. My hands seized the base, and I clutched it firmly for a second. It was soft and flexible but firm at the same time. I wrestled it into position towards my mouth, and it bounced slightly. My lips approached, tongue out, ready to consume. I wet the tip with my tongue in swirling circles and began to cover the head in my mouth. A familiar bitter taste overwhelmed my tongue and nostrils, much like a condom or rubber band.
The cock became slick and smooth as I slobbered all over it to fit my open jaw further down the shaft. She looked amazed. My favorite response to my sluttiness. She put her hands on my head like it was something she had seen in porn and knew men did when they were trying to control the rhythm of their blowjob. I followed her flow and let her control my bobbing with audible gasps and slurps. Since the first time a boyfriend in high school gripped my head like this while I blew him, I both despised the control and loved the act of submission. I reached down and found myself completely wet.
Time passed quickly and slowly simultaneously, and I stopped counting the song's timing. I started to tease myself while choking down her giant strap-on. Gagging, drooling, maintaining eye contact, and giving her the show I thought she deserved. I let her feel assertive and calm in controlling my movements, taking what she wanted. She closed her eyes and moaned as if the appendage was real and pushed her dick into my mouth with her crotch. I wondered if it touched and stimulated her as well or how wet she was, but I didn't want to think about her pussy. I only wanted to know her as a hard cock that I was in service of.
I had command of it now, twisting and gliding from my hand to my mouth with traction, covering the shaft and flowing in one encompassing motion. I continued to touch myself with my free hand. She thrust into my mouth now, more aggressively and with ownership. I rubbed my clit furiously, with intention, and started to cum, releasing my mouth and closing my eyes with one hand still wrapped around her dick. She seemed pleased. Maybe shocked. I hoped it was everything she came for. I instantly never wanted to see her again.
She opened her wallet and handed me the rest of the money inside it. I tucked it into my purse and went back to work.