Banging the Boss

I earn extra cash working as a gay escort. I don’t work for one of those services; I’m strictly independent. I have my info posted on several of the most popular escort web sites, so I get a lot of exposure. My rate is $150 per hour, and I’ve never had a guy complain about my fee. 

I do have a full time job. I work as an operations manager for a local outsourcing company. My job is pretty stressful. I have 25 employees who report directly to me, so I constantly have to deal with their issues. Not to mention, I have to make decisions all day long. 

I started escorting about a year ago. I guess I started doing it because I wanted an escape. And what better escape than getting paid to have sex, right? I put up a few body, dick, and ass pics on a couple of sites just to see what would happen. I never post or send face shots. Pics tend to get sent out and posted all over the Internet, and I don’t want my face plastered all over for everybody to see. And, besides, guys usually aren't really hiring me for my looks. Know what I mean? 

After about two weeks, I started getting emails from potential clients. A normal week for me is about 5-7 clients. I have a few regulars, but most are one-time only hook ups. 

Most of the guys who hire me are traveling on business and want a little company. They’re mostly all married too. I guess when they go out of town they want some of what the wife can’t give them-a big ole dick up their tight ass. If they’ve got the cash, I’m more than happy to bend them over and drive it home. 

I’m 26 years old but look 19. I’m 6’2 and 188 pounds. I’ve got jet-black hair, crystal blue eyes, a smooth body, and a huge prick. My dick is 10 inches long and almost 7 inches around. It’s one of my proudest assets-along with my ass. I’ve got a nice, round, firm, tight, smooth butt that drives the guys crazy. I’m a top only, but I don’t mind spreading my cheeks and letting them have a little lick. I love it. Getting rimmed is one of my favorite things. 

I’m about to tell you a story about one of my hottest hook ups to date-my boss!

It happened about a month ago. I got an email from one of the escort sites from a guy named “Bob.” Bob was a first timer and was looking for a gay escort. I have to tell you, I always jump at the chance with a first timer. There’s nothing better than popping a man’s ass cherry and breaking him in-especially when your dick is as big as mine. 

Bob was looking for a hook up for Saturday night. Since it was only Wednesday, we had plenty of time to make arrangements.

I sent him my standard email with rate information, limits, disclaimer, a couple of extra body and dick pics, etc. He responded the next day and wanted to confirm for Saturday at 8:00 p.m. He sent directions to his house and his cell number. I sent my confirmation email and we were set.

Saturday night rolled around. I left for Bob’s house at about 7:30. According to the directions he sent, he only lived about 20 minutes from me. I knew exactly where his subdivision was so finding the house was no problem.

I found the house and parked in the driveway. The house was gorgeous, and there was a 2003 Lincoln Navigator parked in the driveway. Bob must have some money I thought to myself.

I rang the doorbell and waited for Bob to answer. However, it wasn’t a guy named Bob who answered the door. It was a guy named Steele. The reason I knew his name wasn’t Bob was because I knew him personally-well professionally actually. I was standing on the front porch in a tight, slutty outfit, looking hot and sexy as hell, staring back at my boss. That’s right. My Saturday night hook up was none other than my vice president! You could have knocked me over with a feather. 

I don’t think it registered with him at first. He looked at me with an odd expression and asked me what I was doing at his house. He obviously used my real name because he had no idea I was his trick for the night.

It took a minute, but I finally regained my senses. I didn’t know what to say, so I stuck with the truth. Hell, I mean, he was the one who hired me, right? What did I have to be nervous about?

“Ah, Steele, I’m J.T. We made a date for tonight.” 

J.T. is my escort name, and as soon as I said it, all the blood drained from his face and a look of absolute horror came over his face. 

At first I thought he was going to try and deny it, but he didn’t. He just looked at me and said, “Ah shit! You’re fucking kidding me, right?”

I kind of chucked and asked, “Can I come in? I think we better talk.”

I couldn’t believe it, but he moved aside and let me in the house. He shut the door and we both just stood there looking at each other.

Since I was the “professional” I figured I should say something.

“What do we do now?” I asked.

“Well, we obviously can’t do this” Steele answered.

“And, err…ah…$%#&*, I mean J.T., you have to promise me you won’t tell another soul about this. My marriage and my career could be ruined.”

I knew he wasn’t kidding. His wife was one of our corporate attorneys, and I knew her well. I don’t think she would have been thrilled with the idea of her husband sucking another man’s dick and taking it up the ass.

“I think you should leave now.”

I noticed he said, "I think."

I turned to go, but then a thought hit me. Here was my VP wanting to get fucked for the first time. What better person to pop his ass cherry than someone he knows. 

Instead of leaving, I turned back and faced Steele.

I started, “Let’s stop and think about this for a minute.” 

“Think about what? What’s to think about?” he stammered.

“Well, you obviously want to try sex with a man for the first time, so why not try it with someone you know? Besides, hell, I’m a gay hooker and getting paid, so I have a stake in this too. I’m not exactly thrilled about the idea of my “other career” getting around the office.”

I think he actually considered it for a moment before coming back to his senses. 

“No. Absolutely not! We can’t do this. We just can’t!” 

The words came out, but I wasn’t convinced.

I was actually getting more and more turned on by the thought of fucking my boss. He was only 39, and he was pretty hot. I figured I had nothing to lose at this point, so I thought to myself “fuck it” and went for broke-pulling out all the stops.

I grabbed my hardening cock through my tight jeans. My monster is 10x7, so he makes a pretty big impression (no pun intended) when he starts to get excited. 

As I grabbed my growing bulge, I saw Steele’s eyes move down to my crotch. They only lingered for a split second, but I definitely saw him look. I knew he was mine.

“Look Steele, we’re both already here, and you have my word I’m not going to tell a soul. So why not go ahead and just do it? Trust me, I’m definitely worth the money, and I can guarantee you’ll have the time of your life.”

The more I talked, the bigger my cock got, and I could see the wheels turning in his head. He wanted to do it. He knew he wanted to have nasty, forbidden sex with another man-to suck another man’s cock and take it up his bung hole.

Before he could say no again, I walked up to him so we were standing face-to-face. He just stared back at me and didn’t flinch or utter a sound. Since he made not effort to resist, I took this as my cue to go ahead.

I reached out and started rubbing his cock though his slacks. His eyes rolled back in his sound and he let out a sigh. I leaned in and pressed my lips to his. If I was going to go all the way with my boss, I wanted to make sure he had an awesome time and got to experience the whole nine yards.

I slid my tongue between his lips. He resisted at first, but, finally, his resolve broke down and he gave in to his darkest fantasy. 

He opened his mouth so I could slide my tongue all the way in. He started kissing me back. He was actually a pretty good kisser. I felt his tongue searching for mine. I slid my tongue into his mouth as far as I could and starting giving him a wet, sloppy French kiss. 

He started getting into the scene. He moved my hand aside and I felt him grab my cock through my jeans. While he played with my dick, I reached around with both hands and grabbed his ass. I see him walk around the office all the time and I’ve often thought his ass was hot. Now I was about to see and taste and feel and FUCK for myself.

I was right. His ass was small but very round and very firm. It felt great. I started kneading his buns with my hands. Pulling his cheeks apart and then pressing them back together. I pulled my right hand away and gave him a firm “smack” on his right cheek. He flinched slightly and moaned into my mouth. Then I pulled my left hand back and gave him another “smack” on his left ass cheek. This time he didn’t flinch. He only moaned into my mouth and started rubbing my dick even harder.

I broke our kiss and asked, “Where’s the bedroom?”

He just turned and started walking away as I followed behind.

When we got to the bedroom, I grabbed Steele by the shoulders and shoved him to his knees. I grabbed the back of his head and pressed his face to my crotch. I could hear him sniffing and sighing at my boner. 

“Is that what you want?” I asked him with a chuckle.

“You wanna see my big ole boner, boy?”

I heard a faint “uh huh” as a response. 

I pushed him back by the forehead and stared down at him. He met my stare with a gaze that was filled with pure animal lust. He licked his lips in anticipation of tasting the monster I was still hiding inside my jeans.

I decided to give him some practice, so I sucked one of my fingers into my mouth and moved it in an in-and-out motion. I then took the finger out of my mouth and slid it into Steele’s mouth. He immediately started sucking on my finger as I fed it to him. He was sucking hard too. If he sucked dick with the same gusto, I was the one who was in for a real treat.

I let him suck on my finger a while longer and then pulled it out. I reached for my fly and began undoing the buttons. He just stared at my crotch. It was obvious he couldn’t wait to get a look at, and taste of, my dick.