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The MILF Assistant

by Ms. Christine of

You really are hot for MILF’s aren’t you? You’ve always been attracted to those mature sexy women. Like a deer caught by a wolf, you have always wanted to submit to a Cougar, to let her use you however she wanted! When you saw the posting at work, the one looking for a personal assistant to that hot older woman in the corner office, you just knew that was right for you. Oh, you thought it was going to be the typical assistant job – run for her coffee, keep her files organized, answer the phones. Just being in her presence would be enough. It would give you jerk off fantasies for months, wouldn’t it? You just never realized how “personal” your services would become…and how your fantasies would come true!

The interview seemed normal

You sat in a chair across from her, while she reclined on the couch. You just couldn’t help staring as she crossed her legs, and that high heeled shoe dangled from her stocking encased foot, your eyes roaming up that smooth, sexy leg. You thought she didn’t notice, but she did, a smile came to her red, full lips as she realized, and announced, you’d be perfect for the job. She knew just how submissive you were, and how she’d be able to mold you into the perfect assistant, serving her most personal of needs.

The first few days were pretty much what you expected

Then, one day, as she was speaking on the phone with a client, she pointed to a spot on the floor next to her. You rushed over, and stood there. She covered the mouthpiece for a second, looked at you and said, “kneel there.” Without even realizing you were doing it, you just dropped to your knees. While she continued her phone call, her shoe ran idly up and down your stomach, finally settling in your crotch. You turned red with embarrassment, as you felt you cock growing hard, throbbing in your slacks. When she was finally done, she looked down. “You’ve got quite a stain on the front of your pants, you’d better take them off. In fact, why don’t you just get naked for me.”

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From then on whenever you were in her office you were naked

Then came the day she told you she had a very stressful day and needed some relaxation. She ordered you under her desk, and under her skirt, and just said, “Make me cum, I need to relax.” It was heavenly wasn’t it, licking and sucking on her beautiful pussy, while she hummed, and let out soft sighs and moans, covering your face with her fluids. It became a daily ritual, one you looked forward to every day.

And when did you know she really owned you?

When you slid under her skirt one day and found that strap-on waiting... “Go, ahead, get it nice and wet," she said laughing, “I forgot to pack the lube today.” After a while, she pulled you out from under her skirt, bent you over the desk, and you felt that strap-on nestled up against you hungry, waiting hole, and then she thrust forward. It must have been hard to answer the phone when it rang, as she pounded away at you.

And tonight? Well, tonight, she told you to come to her home, for more personal “mentoring”. You can’t wait, can you?