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There is nothing to fear but fear itself - and maybe getting an embarrassing hickey

Wednesday, 13 August 2014 Written by // T. C. Pomeroy Categories // Dating, Gay Men, T, C. Pomeroy, Lifestyle, Living with HIV, Population Specific , Sex and Sexuality

The Sex Diaries of T.C.Pomeroy continue with the question “Am I that sexy man who can’t get laid in America’s gayest and sluttiest cities?” Not that our T.C. isn’t trying.

There is nothing to fear but fear itself - and maybe getting an embarrassing hickey

"Attention All Rentboy Shoppers" 

Increasingly horny and jerking off more than ever, I decided it was time to give myself a present, to patronize the world’s oldest profession and buy myself a hooker.  It was time for Christmas in July.   

Cruising was a regular habit. I became increasingly obsessed about several different escorts until I narrowed my selection down to two.  The runner up was equally sexy, but since he was local I decided to go with the guy who was visiting, Jesse Santana (below left)/ I’d jerked off to his pornos for at least a couple of years.  His sex was more than just performance, something I believed made me think he would provide me with an night to remember.  Expensive, yes, especially given my cash flow, but I could always pick up extra shifts at work. 

I was initially too scared to contact him but then in a cloud of pot smoke and too much cum in my balls I texted him, asked about his schedule, whether he was shaved or natural, if he was a good kisser and if he wore cologne.  He had free time, his body hair was natural, said he loved to kiss, had awesome lips and hadn’t worn deodorant for years.  Bingo!! 

Then like San Francisco’s famous fog, my anxieties began, rolling down the hillsides of my brain, obscuring my desire. I began obsessing about everything. The cash, my nerves, whether I’d be too anxious to get it up, too pent up and come too soon or that he’d be too tired after spending time with other clients craving his sexy cock and beefy ass. 

The combination of low self-esteem, the cost of an hour as well as the fact that if I started to rely on hookers I might be both broke and crippled, unable to find a satisfying lover, a fuck buddy or just learn how to trick if I had to negotiate the ins and outs of sex, the yes do it like that, or no not that all started to add up. 

I imagine my texts and lack of specifics regarding a hookup time made me seem like a flake or a stalker, something I imagine must be hard to navigate when your pouty ass lips and meaty cock are there for all to see. 

We had made a plan, late on Wednesday, when I was done for work. I texted him mid-evening checking in but when I didn’t hear back I didn’t touch base until I was drunk and stoned, telling him let’s try another time.  When he realized he hadn’t responded to my text, he was gracious, apologized and told me he was game. I declined, blaming my intoxication,  which in retrospect showed me I was too scared to pay to play, to fuck with a pro. 

No More Pussyfooting Around: Time for Action 

What’s more I saw that in truth it was time to take the bull by the horns, the balls by the scrotum and get in on the action. That big-mouthed me, the guy who can talk the bark off a tree or the bronze off a sculpture (unless of course they make me horny) has hidden behind the "sex is too scary" story for too long. That engaging in the dance and sometimes disappointment of requests and refusals is far better than the sad and lonely life of jerking off at home night after night after night.   

So three days later I went to the Berkeley Steamworks. It was 9 pm on a Saturday night. In retrospect I should have gone later. It wasn’t that crowded. The flesh parading around in towels was mostly not my type. The few that were my type left me too afraid to make a move, though I realized without the gift of my mouth I didn’t know the protocol, whether I should touch their shoulder, drop my towel to show them my goods or merely smile and nod.  

Yet it still felt good. I had a great soak in the Jacuzzi and loved the sauna even more. I stayed only 90 minutes but leaving I was satisfied knowing I’d be coming back for more.  

Leaving I texted some friends who I work with, a married straight couple and another gay guy.  They drink and party, mostly cocaine, like it was 1985.  I was tired so I abstained except for some vodka and lots of weed. 

Dark rooms

Heading out at midnight we went to South Market to the Powerhouse, a leather-ish, slutty, scruffy and sexy bar that also has an old school back room.  Located in a small alley-sized space, these days it's filled with smoke (no smoking in any SF bars - only outside) and the smell of sweat and a slight aroma of poppers and cock. The latter may have only been in my imagination but I’m told taste and smell both begin with the eyes and the brain. 

We smoked weed in the cramped back room. It was cloudy with smoke and the smell of sweat, poppers and the occasional sound of a hungry cocksucker slurping on dick. I didnt take part but it was fun being there with my charismatic partying wingman of a pal.  

It had been years since I had gone out with anyone who likes the bar game and it was lots of fun, even before I ran into Jim.  

I was surprised running into him, a guy I have known for twenty-years and always been attracted to.  Quiet, somewhat shy, we’d run into each other now and then, our mutual interest never clearly delineated as platonic or more. His shirt showed off his sexy muscular body, something I’d never noticed before. Massaging his shoulders as we talked, catching up on the years, I wasn’t sure if this was two acquaintances chatting or the prelude to sex.  

When he told me the massage was giving him a boner I felt the bulge in his pants and smiled while I ground my palm into his big hard dick. He had to find the friend he came with and I followed him to the backroom. His friend wasn’t there. We made out and felt each other up.  I thought we had left together but I was wrong.  When I got to the main part of the bar he wasn’t behind me. 

Waiting in the main bar, hopeful that each time the backroom door opened Jim would appear, he never did.  I figured he was looking for something more. More anonymous, more built, more aggressive, something other than me. 

My wing man was missing too so I went a few doors down Howard Street to the Hole in the Wall (above).  My buddy wasn’t there. I returned to the Powerhouse watching two sexy guys make out when Jim reappeared. He came right up, told me he didn’t realize I had left the backroom and that he thought he was talking to me for three or four minutes before he'd noticed it was someone else.  

We started where we left off and I felt grateful that I was able to have a conversation with this man I wanted to fuck. I drove him home. We felt each other up the whole way there. When I asked him if he wanted to hang out he said no, let’s do it another time when it wasn’t so late.  

I had defeated inertia, got out of the house and discovered the baths, an old friend and the fact that sex was everywhere but I’m not sure how I want to get it. 

Am I that sexy man who can’t get laid in America’s gayest and sluttiest cities? Am I a man who loves jacking because I love jacking off?  Or someone who engages in self-pleasure because making a quality connection is hard, especially for a guy who talks to anyone, even strangers, unless that someone provokes his desire. Do hormones make me mute?  

I don’t think so. Even though I was too afraid to touch someone standing next to me in a gay bathhouse or flirt and chat behind the digital wall of Grindr, Scruff and all those digital places where men meet. 

The new era begins now. Time to get sweaty and hard with someone else holding my cock. Time to realize the risks are small and that opportunity is everywhere.