Jessica_(7)

Jessica the Transsexual

I have worked for an advertising agency for a few years now, and recently I took a Managing Editor position in the agency. This was a huge opportunity with all the perks, money etc., that a person could want.

One day when we were having our morning meeting a new girl walked in who was gorgeous. She was about 5’7, exotic, and come to find out she was from Puerto Rico. When she spoke, she had a very sexy accent that was an even bigger turn on.

After the meeting, and I went back to my office I found myself thinking about the exotic Jessica. I knew she was an employee, and office dating is frowned upon so I knew not to pursue it.

Weeks went by, and I stopped thinking about Jessica until one Friday afternoon that I had a meeting with a few people in the department. Jessica walked into the meeting wearing a pencil skirt, high heels and a button down top that was tight and you could tell she had big tits.

She sat down at the table near me and she kept staring me down like I was prey. After the meeting she lingered after everyone left, stared at me for a minute, smiled and then left.

I looked at the table and saw a piece of paper with the name of a club, and the time 9:00 pm. I was so horny for the rest of the day, but had to contain myself. I got to the club at 9:00. As I got to the door I turned around and I saw her slowly walking up in a black dress, strappy high heels and she looked gorgeous!

“You look handsome boss.” I was about to reply, “Shh… I like calling you boss,” as she gave me a kiss, took my hand and we walked inside. After a few drinks and some idle conversation, “let’s dance, boss.” She took my hand and led me to the dance floor.

As we danced she made sure to either press her chest against me and kiss me or turn around and press her voluptuous ass against me and rub against my crotch.

After awhile, she whispered in my ear, “Let’s go to your place boss.” We then left and I followed her back to her place. I knew this was wrong, but she was so damn sexy, I had to have her.

When we got to my place she lead me to the living room where she sat me down, then sat on my lap and starting kissing me. She started kissing my neck, and then started undoing my belt and pants. She then pulled my pants and underwear down and started stroking my already hard cock. “I am glad that I can turn you on boss.”

As she was stroking my cock, she began to lick and suck on my balls, “Want me to suck you off boss?” I looked down at her as her tongue began circling the tip of my cock and nodded.

She then engulfed my cock as I could feel the back of her throat. “Oh shit that feels good!” She began to massage my balls as she was going up and down on my cock with veracity, “I want you to shoot your sweet cum down my throat boss.” She then went back to sucking my cock like a calf sucking for milk.

After a few minutes of intensity, “Oh God I am about to cum!” Right at that moment she stuck her finger in my ass! Despite the shock I could not believe how intense it made my orgasm as I exploded and shook as she massaged my prostate intensifying my orgasm.

Once I finished one of the best blow jobs I can recall, she kissed me, stood up and said, “Have a good night, boss. I will see you on Monday, smiled, and left the room.”

We would hang out on occasion, and she would give me a blow job then leave. I was wanting more, but if that was what she was into then I decided to go along with it. One night while laying on the bed and making out, she said she wanted to fuck, and in my mind all I thought was, “finally!” She got in the reverse cowgirl position on top of my cock and helped guide my cock into her ass! Not quite what I was expecting, but her ass was so amazing and felt so good on my cock I went along with it.

She rode me, moaned and she went back and forth on my cock. After awhile she her moans got louder and from what I could tell must have been fingering herself as she kept saying, “Come with me boss!” Watching her move back and forth was so arousing, and listening to her I eventually exploded as she began to gyrate and cum.

After a few moments, and I was planning to ask her why she wanted me to fuck her ass, she got up, got dressed, kissed me, “Thank you boss, you were amazing.” She then left.

Monday came and she acted like nothing happened, in fact a few weeks she hardly spoke to me, so I left it as a night of fun, and to move on. Then, the on Friday, as I was about to leave there was a note on my desk, and I could tell it was her handwriting.