My Boss

Story Info
Horny older boss makes him work overtime.
1k words
4.32
94.6k
10
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My boss, Jan, is quite a bit older than I am. She just had her fiftieth birthday. I never thought of her in a sexual way before. She is not an unattractive woman, but I certainly would never stare at her ass as she walked by my office. So I wasn't thinking in those terms when she invited me to dinner.

Carrie is a coworker who I do lust for. She has a hot body, pretty blue eyes and long blonde hair. We are good friends, and I would ask her out, but you know how that can be a problem. If the relationship goes sour, then there will be lots of trouble at work. Both Carrie and I are crazy about our boss and we would do anything for Jan. So when Jan asked us to meet at Carrie's house for dinner, we both said sure.

The dinner was eggplant parmigiana which I cooked for the two women. We finished two bottles of wine at dinner and we were feeling no pain. Later, Carrie said that she had to meet with an internet buddy in an chat room and went upstairs to her bedroom. Jan came over and sat next to me on the couch. She pressed her body against mine and it wasn't long before we were kissing. I was shocked. Carrie was right upstairs! Was this whole thing planned?

Jan's kisses were so hot and passionate that I didn't care about the situation. She felt so good. I kissed her back hard, driving my tongue into her mouth. I felt her hand slide up inside the leg of my shorts until she found my already erect cock.

Jan is married and is a great mother to three lovely teen-aged boys. She has a husband who she loves and speaks of often. She has a photo of her family on her desk. So why was she doing this? At the moment I didn't care.

She tore my shirt off and went for the buckle of my belt. I was now in the living room of my friend Carrie's house completely naked with my boss. I undressed Jan. She was wearing a full sized white cotton panty, the kind that somone's mom would wear. It was so cute. She was standing in front of me. I slowly pulled on the elastic of her waistband and folded it down to expose the soft skin between her belly button and her pussy. She was trembling. My tough hard-nosed boss now seemed so vulnerable and fragile. I kissed and licked her working my way lower and lower until my tongue was on her pussy. She let out a loud moan of ecstasy which I'm sure that Carrie could hear upstairs. Then we heard Carrie's voice coming from upstairs. She said, "My internet lover wants to know if you guys are fucking yet."

Jan then grabbed my hand, pulled me off the couch and started leading me upstairs. I couldn't believe it! We were both naked, my cock was sticking out like a flag pole, and we were going to see Carrie! Apparently, Jan wanted to show Carrie what we were doing.

Carrie was seated at her computer wearing a nightshirt, proof that she and Jan had made some kind of plan. Carrie wasn't aware of this part of the plan though. She was shocked when the two of us walked into her bedroom and Jan pulled me on to her bed. My kinky boss was not only a philanderer, she was also an exhibitionist. Who would have thought? I went back down to Jan's pussy and I could hear the keys of Carrie's computer as she typed out a play-by-play description to her internet lover. Jan was very loud. She was whimpering and moaning and was so on fire. I couldn't believe it. It was as if she hadn't had sex in twenty years. She was coming really hard. I knew she needed more, so I slowly inserted my finger into her and started licking her clit again. She was builting to another orgasm and she was almost crying when she came again. I got on top of her entered her. She said, "Oh my god you're so much bigger and thicker than my husband, Oh you fill me so good, Oh my God". I was gushing my cum into her and she was coming again with me.

She pushed me on my back and got on top of me. She was rubbing her wet, swollen pussy on my cock. I could feel my semen dripping down my balls as she rubbed me. She was pleasuring herself as she rubbed her clit on my cock, but it felt so good for me too. I was getting hard again. She put my cock back in her pussy and started thrusting her hips. She was fucking me hard. I have been with a lot of women, but I have never been fucked that hard before. She screamed as we both came again.

She rolled off of me and lay face down on the bed. I went down between her legs and started licking her there. She got up on her knees so that my tongue could reach her pussy. My tongue was playing around in her ass and going down to her pussy and then back up again. Carrie said out loud, "now he is literally kissing the bosses ass." She was groaning again, obviously enjoying the stimulation of her anus. I rubbed her clit with my finger as I licked her and she was going crazy. She came again, really hard. I was on fire for this red hot woman. I grabbed her hips and thrust hard into her from behind. Now it was my turn to fuck her really hard. I screamed myself as I came so hard that I collapsed afterwards.

We held each other for awhile and then my boss ordered me to get dressed. Jan told Carrie that she owed her one as we walked out the door and then Jan went back to her husband and family.

The next day I received a dozen roses at work from and "anonymous" lover and an invitation from Jan to go away for a weekend. I also received a note from Carrie that she enjoyed sleeping in her sheets that were soaked with my cum, that she had to masturbate herself to sleep, and wanted to know when it was her turn.

Life is good.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousover 10 years ago
liked it

Good but needed more flesh to it , more build up

AnonymousAnonymousover 19 years ago
Great story but lot of spelling mistakes

It is a great story, I wish it were longer and more descriptive. Hopefully there is a sequil, but please check your spelling.

AnonymousAnonymousover 19 years ago
Not too bad in all

Not bad, but too short. Be more descriptive. Also, use a spell checker next time too.

AnonymousAnonymousover 19 years ago
more?

Great story, please continue

Share this Story

Similar Stories

Lisa Needs It A big dicked student seduces a big titted teacher.in Mature
Seduced by My Mother's Boss A young man is seduced by bossy older woman.in Mature
Swimmerboy Pt. 01 A young swimmer falls for his mom's best friend.in Erotic Couplings
High School Harem Pt. 01 I'm the only guy in an all-girls school...in Erotic Couplings
Mom's Best Friend: A Virginity Lost Nerd gets lucky when MILF seduces him after seeing his cock.in Mature
More Stories