Love in the Workplace Ch. 06

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Part 6: The Assistant

Since my promotion things couldn’t have been better. Work has been good and the play has been even better. Things have been getting boring and into a rut. There has been a lot of turnover and my work lovers Karlen, Amy and Erin have all moved on and are no longer with the company. Barbara is still there, and we’ll occasionally have “meetings” scheduled in my office, but things aren’t the same. My new job puts me in direct contact with the CEO and I find myself working for him personally on a lot of projects.

On the plus side, this also puts me in touch with his assistant Cassandra, and over the past months, I’ve gotten to know her and we have become friends. Cassandra is older than me, about 8 years my senior, is divorced and is now a single mom to a 15 year old boy. She has shoulder length brown/sandy blonde hair, beautiful brown eyes, tall, about 5’11”, over 6 feet tall in heels, with long legs, a great body and a very sweet voice. Today, Cassandra and I are going to take our work relationship to another level.

On this particular morning I’m working on a few items for the CEO. I finish off a report, put it in an envelope, and walk it up to his office. Cassandra is sitting at her desk just outside the door to the CEO’s office and greets me with a friendly smile. She’s wearing a white matching skirt and jacket, cream colored shoes, and a dark blue blouse. WOW, Cassandra looks great.

Cassandra: Good morning Brad, how are you?

Brad: I’m good Cassandra, just have something here for the boss. By the way, you look stunning today.

Cassandra: (blushes) Why thank you Brad! That’s so sweet of you to say.

Brad: (smiling) I have to get back downstairs. It’s going to a busy day. See you later.

I go downstairs and head back into my office and close the doors. Damn, Cassandra looks good. I really want to drop ’em and rub one out to her, but I’ve got a lot of work to do today so that Escort Bayan would have to wait. I’ll put Cassandra in the spank bank for later. I spend most of the rest of the morning finishing another report and run it back upstairs to Cassandra.

Cassandra: Back again?

Brad: Yeah, something else for the boss.

I drop off the envelope and head back downstairs and continue my work. I finish off the last thing I need to complete and go to drop it off upstairs before I head off to lunch. I get upstairs and Cassandra isn’t there. Thinking she’s gone to lunch, I drop off the final report in the CEO’s inbox. I hear a door open behind me and see Cassandra exiting the ladies room.

Cassandra: Three times today? You know Brad, you could have just dropped these off in the interoffice mail.

Brad: But then I wouldn’t be able to see you.

Cassandra walks up behind me, stands directly behind me and talks into my right ear.

Cassandra: I know all about you Brad. Are you looking to get up my skirt? Or are you just looking for jerk off material?

Brad: Cassandra! No. Absolutely not! You’re the CEO’s assistant. That wouldn’t be appropriate.

Cassandra: From what I hear, your concept of appropriate is a little different from everyone else’s.

Cassandra reaches her right hand around and grabs my crotch and feels my stiff penis through my pants.

Cassandra (whispering into my ear): Well, someone is not telling the truth. Is it you or him?

Cassandra reaches around, unbuckles my belt, unbuttons then unzips my pants, she opens my trousers and pushes my underwear down, exposing a rock hard and erect penis. Cassandra then wraps her fingers in her right hand tightly around the shaft. I let out a long sigh.

Brad (whispering): Oh my.

Cassandra whispers into my right ear.

Cassandra: Do you jerk off to me Brad? Don’t lie to me, because I’ll know.

Brad: Yes.

Cassandra: Etimesgut Escort Do you like being exposed like this?

Brad: Yes.

Cassandra: Do you like what I’m doing?

Brad: Yes.

Cassandra lightens the grip on my penis and starts to slowly run her hand up and down the shaft of my penis. She uses her left hand to unbutton my shirt as she runs her hand across my chest, playing with my nipples with the tips of her fingers as I let out a long soft moan.

Brad: Ohhhh Cassandra.

Cassandra: I know you like having your nipples played with? Do you enjoy my touch?

Brad (breathing heavily): Oh yes.

As Cassandra continues to pump me, my pants and underwear start sliding down my thighs and fall all the way down to the floor wrapped around my ankles. She’s nibbling on my ear and kissing my neck when I turn to the right to look at her. Our eyes meet as our lips meet in a long and passionate kiss. She follows up with a few short tender kisses on my mouth, chin and neck as her left hand roams across my chest and inner left thigh. I softly whisper to Cassandra as special request.

Brad (begging): Cassandra. Please. Finger me up my asshole.

Cassandra’s left hand rubs my left thig and moves to my ass where she caresses both cheeks.

Her middle finger slips in between my legs, as she teases me just outside my asshole before she slides it up my ass.

Brad: Oh god Cassandra, that feels so good.

This whole time, people are starting to return from lunch and, like my first public act of love with Karlen, a crowd starts to quietly gather. Cassandra sees this and starts to get more aggressive with me.

Cassandra: You like getting it up the ass, don’t you Brad.

Brad: Yes.

Cassandra: Say it

Brad: I like getting it up the ass, Cassandra.

Cassandra takes her middle finger out of my ass and switches hands. Her left hand Ankara Escort reaches around and replaces her right on my erection as she runs her right hand up and down my body. Her right hand caresses the inside of my right thigh, then up and down my body as she plays with my nipples again, then runs her hand along my ass. Her middle finger makes its way up my asshole, this time with a little more depth. I can feel her curling her finger inside of me, trying to reach for and tickle my prostate. I look over to my right again as the two of us engage in more kissing, this time with more passion and tongue.

Brad: Oh my God, Cassandra, I’m so close.

Cassandra: Do you want to cum?

Brad: Yes, Cassandra. Yes.

Cassandra: Convince me. Tell me something that would want me to make you cum.

Brad: I’m in love with you Cassandra. I have been since I first met you and saw you. I’ve wanted you for a long time. I want to cum to honor you as an expression of my love for you.

Cassandra saves the best for last. She loosens her grip with her left hand, lifts her index finger and places it right along that wonderful vein just below the head of my penis. She rubs it softly and gently using small circles when the sensation becomes too much for me.


We continue kissing as I’m moaning and screaming out her name.


My penis starts pumping out semen as I can feel the intensity of the orgasm run from the head of my penis all the way throughout my body. Cassandra doesn’t care. She lets my cum shoot out and land on the carpet right in front of her desk as she continues to milk me dry.

After my orgasm subsides and my ejaculation finishes, Cassandra reaches for a kleenex on her desk to wipe off her hands. She walks back to her desk, sits down and goes back to work as if nothing happened, answering phones and checking email. Meanwhile, I’m standing in the middle of the room with my pants wrapped around my ankles and cum on the floor and dripping from the head of my penis with a captive audience.

Wow what a wonderful experience. This is definitely going into the spank bank.

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