The Man I Was

As I walked up to my new office I glanced over at the name on the door. Michael James. I go by Mike, but I liked how official "Michael James" sounded. I was moving up in the company, and I had my first office. In a world of cubicles an office is pretty close to heaven on Earth.

Sitting down at my new desk I took the newly framed picture of my wife, Shannon, and our son Jacob out of my bag and placed it to the right side of my monitor. The silver frame clashed a bit with my black monitor and I thought to myself that I should switch back to the black frame I had before.

As I pushed the button to turn on the computer I couldn't help smiling. Things were finally falling into place. As I was sitting there with a stupid smile on my face, my secretary Anna walked in to my office. Well, she wasn't specifically my secretary since she was shared by a couple other VP's, but nevertheless she was my first.

Anna was a looker, but not in a conventional way. Living in Minnesota you get used to a certain type, and a latina sort of stands out more than most. She dressed impeccably well for a secretary, or at least compared to some of the others in the office who were a bit more frumpy, and although she wore a bit too much make-up for my liking the combination of her tits and ass made for a wonderfully enticing package. Unfortunately for me Anna would be leaving us in a couple weeks to move back to Texas.

Anna and I got along pretty well right off the bat, the fact that she was married made me a tad more uninhibited around her than I would be normally. It makes it much easier to flirt when you don't think it's going anywhere.

My marriage was actually going very well, but like most of my friends after awhile I got bored with the sex. I missed the excitement that comes along with meeting someone new and sleeping with them for the first time. In a marriage the sex gets rather bland and scripted after awhile, and my marriage is no exception.

Well, the two weeks came and went and it was time for Anna's going away bash. We were all planning on heading over to "Monk's" bar and most of us decided to walk over since it was relatively close. I wasn't really planning on drinking much since my wife couldn't make it out that night, and needed the car in the morning, but once the beer started flowing I found myself drinking a lot faster than I planned.

Around 11 people started filtering out the door and pretty soon there was only Anna, myself, and a couple stragglers who were more interested in talking baseball than hanging out.

"So, you think we should get outta here?" I asked, kind of hoping she was game for hanging out a bit since I was still feeling pretty drunk.

"Whenever you're ready. I figured you could walk me back to the parking garage."

"Okay, but I have to sober up a bit first, I'm going to get a couple waters and hang out for another hour or so. If you want to leave though I'll walk you over to your car."

"I'd like to go, c'mon, we should sober up on the way. It's getting cold anyway."

Although I was diappointed in her decision to go, I knew I should be getting home anyway, and I figured worst case scenario I could sit in my car for an hour or so listening to talk-radio. After grabbing our coats we walked down the street and I placed my arm around Anna trying my best to keep us both warm. Playfully I began to lower my hand until I finally had it resting on her waist and and then when no objection followed I let it fall down a little more until my hand was resting on her ass.

"What are you doing?" Anna asked playfully.

"Listen, it's your last day, can you fault me for cupping that wonderful ass of yours?" I responded as I gave her ass a playful squeeze.

"Cupping?" Anna responded. "Is that what you call it. What would your wife think of you cupping my ass?"

"She would probably cut my dick off, but I'm never going to see you again and I just couldn't live with myself if I didn't at least touch it."

With that Anna stopped and took her left hand reaching down to grab my dick through my pants, "What makes you think I won't cut it off."

"Taking risks is what got me the corner office, why stop now?"

With that Anna grabbed my hand and led me over to the storefront and with my back leaning against the brick wall, and with my dick growing stiff in my pants, Anna lifted her mouth up to my ear and whispered seductively, "I'm a married woman."

"And I'm a married man." I responded not quite sure where she was going with this.

After that Anna started walking again and I hurried to catch up. We walked side-by-side for the rest of the way without exchanging another word. I think both of us were assessing just how far we wanted this to go. It was awkward, but at the same time it was exhilerating to be flirting again so much more openly than the fluffy exchanges we shared in the office. After another 4 or 5 minutes we reached the garage and I finished walking Anna over to her shiny black SUV.

"Okay, well I guess this is where we say good-bye," stated Anna rather matter of factly.

"Yeah, any chance for a kiss good-night?" I asked trying to push the envelope just a tad farther. I still wasn't sure I even wanted this, but I had gone this far, and I knew I could stop with just a kiss. Kissing wasn't really cheating anyway. Besides Anna was gone after today and nobody would be the wiser. Well, any thoughts about pulling out of this thing disappeared quickly as Anna moved in and within seconds had her tongue darting around inside my mouth. As we were kissing it ended up being Anna pushing the envelope as she pulled my zipper down and started fishing around for my achingly hard cock.

I was in shock. Absolute shock. Part of me felt like she was teasing, but Anna began undoing my pants and soon had them pulled down just enough to where my cock was now reaching out the top of my boxers. At this point I knew the teasing had ended, and that this was going someplace dangerous. I didn't expect this, I like to plan things out and I hadn't seriously planned on cheating on my wife tonight. At least I hadn't expected things to be going this far this fast.

In what would probably be the last moment where I could have stopped all of this Anna dropped down to her knees. Her tongue darting out to tickle the tip of my penis just like it did when she first put her tongue in my mouth.

She started sucking, slow at first, and then faster, She was rotating around and finally started working on getting th entire 6 inches down her throat. I placed my hands on her head and I just started letting them feel the pace of her head as she moved back and forth. "Oh, fuck Anna." I gasped. "Suck my fucking cock."

"You like having your secretary suck your dick. You know if I wasn't leaving this would be sexual harassment."

"Oh my god, just keep going."

She kept going, and I was getting close. I could feel my dick growing and I knew I was going to blow. I wanted to blow my load in her mouth so badly, but Anna had other ideas. She pulled it out just as I was about to cum and she started jerking me off furiously and within seconds I was blowing the biggest load of my life in and around her open mouth. As I continued unloading she started rubbing my cock all over her face, and she took it back inside to suck out the last of my juices. Her face was glistening and I just kept staring down at this angel that had given me the hottest blowjob of my life.

Anna then rose to her feet - pulling herself up by the sides of my jacket - and when she was back on her feet she grabbed the back of my head and started kissing me. She had cum all over her face, my cum, and she was kissing me. I had never tasted my own cum before, and hadn't planned on doing so any time soon.

It wasn't much, but I noticed the taste was a tad salty. In the back of my mind I started to imagine what I looked like with the same cum-coated sheen on my face that I had been seeing on Anna's face seconds earlier.

"Oh, fuck Anna. That was fantastic." I stated when we finally broke our embrace. We both looked each other and started laughing. Anna leaned back away from me and then came back in for one final deep kiss, before pulling away and stating, "Your turn," as she started to slide her dress up.

"I'm sorry, I...I...I have to go. I don't mean to be an ass, I don't, but I just lose interest after I cum and I have to get home before Shannon starts worrying."

I know it's lame, but I lose interest pretty quickly after cuming and at the moment I wasn't much interested in going down on Anna.

"Maybe I should go home with you." Anna responded, her tone getting more serious.

"Anna, listen," I started putting my hand up to the side of her face, "I hate to go home, this...I mean, we could do something tomorrow if you wanted." At this point I just wanted to get out of there. Her tone was worrying me, and going home would give me a chance to reassess what I wanted to do.

"Get on your fucking knees, or I'll call your wife and let her know your on your way. Does that sound like a plan? Now, keep being a gentleman and get on...your....knees." She let those last three words hang for a between each one.

And I did, I suppose there are worse punishments for having your dick sucked than going down on your secretary. I dropped to my knees, Anna skirt was already hiked up a bit, and as I was going down she pulling it up a bit further. As I reached up around her waist I wrapped my hands around the sides of her black lace panties and noticed pretty distincly she had an abnormal bulge in an area that is generally bulge free.

I guess in the back of my mind maybe I had an idea of what was going on, but I continued to pull them down and when I did a cock fell out from between her legs.

I fell down from my crouched position onto my ass, as my ass hit the ground my head came to rest against the car parked directly behind us, "What the fuck, Anna. What the fuck is THAT?" I asked almost sounding like I didn't know what a cock was.

"What do you think it is."

"I mean, I know what it is, but how." I stammered, I was well aware of a what a transsexual was, or was supposed to be, but having no experience or encounters in my life I guess I just always assumed they were manly, or at least certainly nothing like this.

"It is what it is, and it is what you're going to be sucking on in a minute." As she finished her statement she moved in, I was now sitting down with my face right in line with Anna's cock as it approached my closed lips. Anna started rubbing it against my face, and I just sat there moving head from side to side. I was still in shock. "Open that fucking mouth Mike." Anna demanded.

It was strange it felt so soft, and light against my cheecks as it rubbed up against them. Part of me wanted to leave, but part of me was getting turned on. After all it was still Anna, the woman I lusted over for so long. Hearing her talk to me like that, like I was her bitch was turning me on.

"Open your mouth Mike or your wife is going to get a call." Anna demanded.

She took one final stop closer and the head of her cock was just inches from my mouth. This was a do or die a moment, a moment that defines a person. I had so many thoughts, but so little time to really do anything about any of them. I couldn't stop staring at her cock though, her completely shaved cock and balls, and it looked so different from mine. It was about the same size, but it had more veins, and looked much smoother.

"Do you like what see Mike?" Anna inquired softly, her tone was less demanding now probably because she noticed how my attention had shifted from shock to just a wide-eyed stare.

"Yes. I think I do, but....." My words sort of trailed off as I looked up at Anna and still tried to absord what was happening.

My whole body was on fire, not from passion, but nerves. I was embarassed and turned on, and confused all at the same time. I had so many different emotions running that I think my body was overloading. Was I gay? Like most guys I had thought about sucking cock a few times when I was jerking off, but I never envisioned it being a possiblity. I couldn't deny that having Anna's cock so close to my face was exciting though, it was an excitement that I had never experienced before.

With that Anna stepped closer, her cock was hard and standing straight out. My own cock had an upward curve, but Anna's was straight as a ruler. The veins were clearly visible and I felt like I could hear it throbbing, although that was probably just my own heart.

Anna's demeanor had changed slightly, she took her hand and was now running it through my hair. "Please Mike, just try it. Take it in your mouth."

I then moved back up to my knees and I moved in and wrapped my lips around just the tip. It was more of a kiss than anything, but I tasted precum for the first time. After moving back off the dick for a moment, I finally took the big plunge and wrapped my mouth around his cock.

I moved my head back and forth now, I had Anna's cock in my mouth and it was new to me, but I was enjoying it. My own cock had rebounded quicker than it had in years. My cock was straining again against the barriers of my pants. I now felt like this was something I had to do, and I wanted to do well. I just kept sucking, I tried doing it the way so many women had done for me in the past. I wanted to be good, after years of bad blow-jobs from my wife I think I it was a matter of pride that I wanted to excel in sucking dick.

Anna's hand was now grabbing my head and she pulled me back, removing my mouth from her cock brought me back to reality for a moment. It was almost like she wasn't there before that, I had become so focused on sucking her cock that the she all but disappeared. Looking down at me, she uttered, "That's it Mike. You're a good cocksucker. Do you like being my little cock sucker?" Her tone was almost condescending, or mean.

"I....I love it." I managed to stammer, it was odd to be looking up at someone like this, in this situations. It felt foreign, like I wasn't in control at all. With that Anna took my head and moved it back to where I had my lips wrapped her cock. I increased the pace, sucking harder, and trying harder and harder to help her cum.

"Do you want my cum. Do you want to feel my cum in your mouth?" Anna said.

I didn't slow down at all, it hardly mattered that Anna was speaking to me.

Anna then pulled my head off of her cock and looked at me, she looked different, she had a wicked grin on her face now. "Tell me Mike, tell me you want my cum."

"I do."

"Say it, say you want my cum." Anna was again back to making demands.

"I want your cum." As quickly as I said it I jerked my had back to her cock.

I went back to work like a man possessed, my head was flying up and down her pole, until finally I could feel it growing ever so slightly. I knew the change, and I knew she was close. I kept sucking, and finally she exploded, her cum was now filling my mouth. It was salty and thicker than I expected but I loved it. I loved feeling the texture of it in my mouth, and loved swallowing it.

"You're a little cock whore aren't you Mike. If you weren't acting so nervous I would swear you've been doing this your whole life." Anna stated while giggling a little bit and now looking down at me as I collapsed back onto my ass and against the car parked behind us.

I wasn't sure what this all meant. Was I gay? I was sitting there with the taste of cum in my mouth, and I just watched as Anna put her cock back in her panties and pulled her skirt back down.

"It's normal Mike, you're not the first straight guy to go down on me. It happens a lot more than you would think" Anna said, I think she realized how uneasy I felt and I suppose this was her way of letting me know that I'd be fine.

I looked back up at her again, with an awkward look on my face, and I just couldn't think of what to say. "I'm married."

"I know, and I'm not. It's just easier if I tell people that I am. C'mon, get up." Anna responded, sticking her hand out to help me to my feet.

"Does everyone else know?" I asked.

"Know what? That I'm a transsexual. Nobody knows at work, this has been a long process Mike I didn't just make the change yesterday. Listen, you should clean yourself up and head home." Anna replied, while leaning in for a kiss on the cheek.

"Will I see you again?"

"No. Try to stop analyzing this Mike, this doesn't make you gay." That was the last thing Anna said as she turned and got into her vehicle. She could obviously see me struggling to comprehend it all, and her words didn't do much to alleviate all those conflicting thoughts running through my mind. There was honestly so much more I wanted to ask her, but it was all too much. There I was standing in a parking garage with my shirt untucked, and a stupid look on my face, and the only thought running through my mind was that I wanted more.