A Moment, A Fling, or A Lifetime?

So I have been crossdressing in private for years and I have just now been able to admit to myself that I want to be feminine, I want to be a woman, and I now really want to be with a man. I have been playing with a few toys in my bum and it feels wonderful.

With new fashion styles and more unisex offerings, I've been wearing some less than masculine clothes to work and I do think some people notice. I just want to go full on fem someday and I wish I had the guts to do it.

Now as far as being with a man, I soooo long for that. I wonder all the time what a man's firm hand would feel like caressing my legs. I wonder what it would be like to be kissed by a man. I wonder what it would feel like to have a man's rock hard cock inside me stroking my hole. And I often wonder what a man's cock would taste like and feel like in my wanting mouth.

One man that I see every day is my boss and I must admit I look at him with lust in my mind. He is tall, slender with blue eyes and blonde hair. Good build and really cute. Two things about him though... He has a real hardon for me and not in a good way. I'm one more write up away from the soup kitchen. But the second thing is, even though he is married, my gaydar goes off around him and not just because I want him. I just have a tingle.

So with Halloween coming up I have so decided to throw caution to the wind and dress up for the office Halloween costume contest. I just have to. I decided to go as a sexy kitty. I put on some of my silkiest black pantyhose, I slipped into this cute but very short black slip dress. Of course I attached a tail! I did my makeup perfectly, a little splash of perfume for a fem touch, then I slipped my feet into some black patent stilettos and off to work I went.

I usually stop via drive thru for a cup of coffee but today I park and strut inside! A wiggle of the tail and off I went, coffee in paw. I heard a man whistle and although i was nervous I also felt a little boost of confidence. Now I pull into work and omg, I just burst out of my car and I strut inside. Now I must have really done my makeup great because no one seemed to recognize me and I got stopped by security to verify it is me. So basically the cat is out of the bag, or maybe in my case the closet!

I saw the boss in down the hall past my desk so I decided to go say hi. As I approached it seems like his eyes were just fixed on me. But I couldn't get a good read wether this was good or bad. But at this point I kinda didn't care. I walked up, said good morning in a cheerful way, spun around and strutted away with a perfect, but not overdone wiggle in my hips that made my tail sway. I just wish I knew if he was looking, but I just strutted back to my desk. For the whole morning people passed by and I got so many compliments, some guys harassed me in a playful non sexual way. One of our out gays said he kinda had a feeling about me. I told him I'm just having fun, but inside my lust for a man just grew 100 times more. I was feeling free and liberated until...

The overhead page summoning me to conference room B. Conference room B is remote, seems soundproof and close to an exit door just past a security office. This is where you get yelled at, written up, or fired. So I grabbed my purse. Yes I used a purse today! Then I made my way to the room of doom. The door was open and the boss was just sitting there with paperwork on the table. He gave a yell for me to close the door which I did as I fumbled a little with the door handle, on purpose...

He stood up and told me to sit down. Of course my eyes looked down to that nice package area, duh... And I strutted over and instead of sitting across from him I sat down next to him after pulling the chair out twice as far as I needed. He sat down and I slowly gave him a leg cross to behold, and I saw him glance down at my legs when I did it!

He gives me the evil eye with a smirk and tells me this is about my costume. I cross my legs the other way in silence and you can hear the nylon rub. I started to say something and he reached out with one finger, then gently places it on my lips. He then tells me he loves it holding his finger in place. I pucker ever so slightly and he drags his finger down across my lower lip. I ask him how much does he like it and he smiles and says a lot! I smile back and throw caution to the wind again. I tell him I think the bulge in his pants likes it too! He turns red and looks down and I immediately say, don't look down, look at me! He brings his head back up and instantly leans in and kisses me. Now I'm the one flustered as he pulls back leaving me with my mouth open as an invite for another kiss which he comes back for. His tongue was dancing in my mouth and I was in bliss as no man has ever kissed me yet. We are now full on making out and he pulls back. He is worried someone could walk in and I just smiled. Remember when I was fumbling around closing the door? I locked it! Upon hearing that he smiles as he leans in to kiss me again, this time bringing himself closer and now running his hand on my silky smooth legs. My legs quivered at first as this is all new to me but then I really started to enjoy his touch. With our mouths locked, his tongue in my mouth, and his hands caressing my legs, I was getting ready to pop, but I think femininity kicked in. I then reached down for what I wanted and unbuckled his belt, opened up his pants and started sliding them down. His cock was already rock hard. It was a beautiful 8 incher, veins popping, not too thick but definitely a hot piece of man meat.

I lustfully dive in mouth first onto his cock, trying to swallow it whole and immediately gag. Rookie mistake! He chuckles and I look up at him and smile. Then I go back lowering my mouth over the first 3-4 inches of his cock this time and close my juicy lips around his shaft. This is a great moment for me! I start moving my mouth up and down the hard shaft of his cock and I feel like I've been waiting for this my whole life. I never realized how soft and velvet like the skin around a cock was and found this to be very appealing. I continue to stroke his cock with my mouth taking more and more in with no problem. I start stroking the base of him with my fingers. All around me is lost as I am completely engulfed with the notion I am finally giving a man head! I do hear some faint muffled moans from him but other than that my entire focus is on his cock.

The next lustful moment I have been waiting for now happens as he shoots a huge rope of cum blasting the back of my throat. It catches me by surprise but my reflexes allow me to swallow immediately so that makes me just want to keep taking it. I keep stroking his cock with my mouth as he just pours his cum in my mouth and throat. It was more than I thought and some started leaking out down my chin a little as I pull off of his cock. Some cum starts dripping along his shaft and I just dive in like it's instinct and lick it off. I see a bead of cum on the top of his head and I dive in taking his whole cock into my mouth. I tighten my lips around the case of his cock and pull my mouth up his shaft milking every last drop of his cum out of his cock and into my mouth. As I reach the tip I just kiss his cock like I was thanking it for my blissful moments.

I got up and sat in my chair as he zipped up. He sat down and as I started to say something he took the papers in hand and told me we still have some business to attend to. My mind was spinning, is he still going to fire me? He reaches forward and guides my hand to a piece of paper folded in half. In it is a key card. He then tells me he will clock me out at 5, leave now get a few cute outfits and meet him at a hotel. He will be leaving after lunchtime. Wow! Heck yeah I'll be there! Without saying a word I get up and start walking out the door. In the doorway I turn to him and say for lunch, eat oysters! I smile and spin forward walking out the door to the exit, and some cum was still on my chin! Stay tuned for part 2!