The Backroom and the Boss

I had a light work schedule over the summer while working for a small accounting firm with a lot of free afternoons. Most days is was just me and my boss since our busy time was the year end and tax season. Officially, I used the short days to work on my writing and art but well, unofficially I spent some of those afternoons in the backroom of a nearby adult bookstore. I had a deep affection for glory holes and backroom trysts. Between the quick anonymous nature and inherent forbidden wantonness of the encounters only added to my attraction to them. There was just something about sucking off some stranger through a hole in a darkened booth that turned me on. Then there were those special shared times with just me an another guy in a that tiny space trying to fuck work without getting caught.

So one afternoon, I had just finished giving a blow job to a hot blue collar daddy in a mechanics uniform when I walked out of the back room. I pushed through the heavy curtain hiding the back room and almost straight into my boss. Talk about being at a loss for words. He was standing there with a DVD titled “Busty Asian Beauties” looking like a deer in the headlights. In a thousand years, I never would have expected him to find in an adult bookstore. Extremely reserved in the office, he had always come off as something of a prude with the wife, kids and church membership. I mean, I don’t think I’d ever seen him in the office without a tie.

With nothing but a quick nod, I quickly exited the bookstore as he stood there. I went to sleep with my stomach in nervous knots as to how the conversation the next day would play out. Though in the back of my mind I did start to entertain a fantasy of two. I would have loved to give him more relief than a mere DVD could offer. Hell, he could watch the DVD at his desk while I was on my knees sucking him off. At a couple years over forty, the man was trim, worked out and sexy as sin despite his conservative bearing. The light beard over angled cheekbones, salt and pepper hair and intense dark eyes just kind of made him really hot. I had to stop myself from day dreaming about him once or twice in the past.

That conversation was nothing like I could have ever expected in this lifetime or any other. Quietly and with a fair amount of hesitation he asked what was behind the curtain. For the first time in my adult life, I blushed as I stuttered my way through explaining the back room. I said there were different booths with different sizes. I emphasized the preview aspect of the booths with some being larger with couches for guys and their girlfriends or girls they picked up on the side. I didn’t bother mention that I’d never actually seen a woman in the backroom.

The next line of questions was even worse, about glory holes. I guess I was his own personal Google or he couldn’t figure out how to turn off safe search. He always knew I was gay so maybe he felt more comfortable asking me than the internet? I didn't know so I gave him an overly generic description with the idea that straight couples used it for excitement and to show off. Again, I left out the part where horny guys went there for quick relief from eager and anonymous male mouths on the other side of the hole. I was so glad when that conversation ended but I knew what images I would be jacking off too that night.

So one day a week or so later, I was getting ready to head out when he asked if I would well, show him the back room. He had been thinking about going but was too nervous to go back there by himself. I didn’t know what to say other than to agree.

A short time later, I led my boss into the back of the adult book store. I bought him a bunch of tokens and took him to a ‘couples’ booth with a couch and widescreen tv. I figured I could plop him down on the couch and make a quick exit before I tried to molest him. Just the idea of being in a back room with him watching porn together made me start to fantasize. The visual in my head of blowing him in a private room while he was still in his Brooks Brothers button down work clothes was an oddly erotic turn-on.

Once we were ensconced in one of the deluxe preview booths I just sort of sat there in awkward silence while he flipped through the videos. He stopped on a compilation of gay glory hole videos. Of course he did. For the next ten plus minutes we both kicked back and watched as a hot porn star sucked of a series of random men without ever seeing who they were. Honestly, it was kind of the hot. It was the forbidden anonymous sex I actually came to the back room for.

Turning to me, he asked me point blank “Can I watch you suck someone off like that?”

Well, that wasn’t at all what I kind of expected. I was sort of thinking, even hoping, he would ask me for a blow job but this… this held promise.

A few minutes later we were in another smaller booth with a glory hole. He stood while I sat on the small bench by the hole. Even in the darkened booth with the only light from the video screen, I was so close I could see the outline of his semi-hard cock but I was unsure if he wanted to participate or just watch. I opted to wait and see what happened. We didn’t have long to wait.

In the darkened hole someone entered the booth and a video started as his tokens dropped into the coin slot. The man was rubbed himself through his jeans in the flickering light from the video before taking out his cock. It was a good 7-8 inches with a nice head. I quickly gave the signal and the dick came through he hole.

Looking up at my boss, he expression was one of conflict and desire. Without breaking eye contact, I took the cock into my mouth and started to suck. I’d always liked sucking dick and this was a great one. Leaning forward, I closed my eyes to more fully swallow the cock which felt and tasted wonderful. Knowing my boss was watching was a huge turn on. My super conservative boss was standing above me as I sucked off a stranger through a glory hole. By now my dick was so hard it was uncomfortable.

Focusing my attention on pleasuring the man on the other side of the wall, I swirled my tongue around the head and jacked him a bit with my hand. I could tell from the copious amounts of dick honey already oozing, this guy was not going to last long.

After only a couple minutes I felt the eruption in my mouth and I did my best to swallow it all of the salty goodness but a bit dribbled down my chin. The cock quickly withdrew and was gone in seconds. Looking up at my boss in silence, I wasn’t sure what, if anything I should even say. Though I could see the outline of his very hard cock through his pants was far more pronounced than a few minutes ago.

He reached out to wipe a bit of the leakage from my chin with his thumb before rubbing it over my lips. Without even thinking about it, I opened my mouth and gently sucked his thumb clean. Looking up to meet his gaze, I saw the lust and hunger I felt reflected there.

Without breaking my gaze or pulling his thumb out of my mouth, he used his free hand to slowly unzip his slacks. His rock hard dick almost exploded out of opening. It was probably a tad over eight inches with huge head and just a drop of precum at tip . He slowly jacked himself while I continued to suck his thumb and watch his expression.

“Open your mouth.” He whispered in quiet command.

Pulling back from his thumb, I opened my mouth so he could feed me his load. With our eyes still locked and my tongue just barely touching the tip of his cock, he came with a rough groan. Spurt after spurt of his load filled my mouth. It was warm, a tiny bit salty and wonderful as I swallowed it down. As his orgasm subsided I gently sucked just the very tip of him to get the last few drops of his jizz. Still breathing heavily after shooting he finally spoke.

“I really, really want to watch someone fuck you.” He whispered.

To be continued...