Joyriding with my Executive Assistant’s Daughter [MF] [M]

Spice starts after the *

As mentioned previously, I once worked for a big bank and was awarded several promotions pretty quickly. Prior to leaving the bank I was running a big department and one of the perks of this position was my very own Executive Assistant who helped me schedule my calendar, manage my time and travel, and screen out the weirdos. As described earlier, she was old enough to be my mother, probably in her early 60s and her name was Donna. She was tiny and Portuguese with short dark hair, a twinkle in her eye and a big laugh. And she was incredibly effective.

It was Donna who witnessed Tina stumbling disheveled out of my office in the aftermath of her wild mid-afternoon orgasm (Mentoring the Nerd). I felt that Donna’s jaw dropping disbelief ruined her impression of me that day.

I assumed incorrectly.

A couple months after the Tina episode, Donna set up a one-on-one meeting with me in my office. Considering that we basically worked hand-in-hand all day, this was highly unusual. I suspected that Donna was going to resign or retire. Read more »

Workplace Harassment Pt 5 (MF impact play connoncon over 30)

“I need someone to stay an hour late with me after close, so I can hop on that conference call,” Glenn announced to the floor at large Friday morning before open. I saw everyone avoid looking in his direction – technically, it wasn’t any hardship. This happened pretty frequently – no one was allowed to be in the building alone, so about once a month we had to buddy up one hour late, or open an hour early. You got paid for the extra time and whoever wasn’t actually on the call could do as they pleased.

“Come on, guys. It’ll be OT, and we’re heading down into the weekend anyway”. I sketched two fingers in the air in a salute; I didn’t trust my voice not to squeak or my arm not to tremble if I raised it. Pointy teeth flashed from across the floor, and a double thumbs up. “Thank you, someone wants to get paid.” My skin felt chilled like I had stepped into a freezer. Once again that not-knowing of what I wanted made my heart feel as if it leapt back and forth from one side to the other of my ribcage. Did I just want to watch him from yards away on his phone, while I read my book under my desk, or my romance novels on my phone? Did I want him to pounce as soon as we locked the door on everyone else? The problem was the fear sat side by side with the desire and I did not enjoy that uncertainty. I didn’t like that he could have that affect on me. Read more »

[M19F19][Anal, dubious consent][shy] Hazel Chapter one

This story is a work of fiction. All of the characters are over the age of 18.

This story contains dubious consent. This is the first chapter and more will be released as they are completed. There’s a complete list of my stories if you go to my profile and looked at the pinned post.

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Hazel wondered what to pack for her three day trip. For certain, she would need her jersey. She wasn’t sure how much underwear to pack. Should she pack a bunch of extra pairs? What if something happens? She didn’t want to have to find a clothing store.

She went over similar calculations with other clothing. Would it be better to pack skirts? Did she need a sweater? It was fall and the weather was getting colder but it wasn’t quite that cold yet. Definitely much warmer than it would have been in her native Sweden.

Hazel was studying abroad in the United State. Naturally shy, she had trouble making friends and making a social life. She was very quiet and she was self-conscious about her accent. Read more »

Lisa Loses her Virginity part 01

It was early in the summer vacation, and I was enjoying the time off. I teach at an all-girls school and am blessed to see hot teen vixens every day in class. I have made it a rule never to fool around with them, even though some of them seem to be teasing me, tempting me to fuck them. I came close to fucking a student but got by the student part on a technicality. My cock started to stiffen as I recalled that time, two years ago.

School had been the usual routine, nothing too special. There were of course the hot, sexy vixens who were made for fucking and sucking. One of them, Lisa Bowles, was 18, and ready to graduate. She was very hot, 5’9″ tall, a solid 145 pounds, with luscious tits, a fabulous ass, and a nice wide set of hips. She was a green-eyed redhead, with a shoulder-length mane of light copper-colored hair, and eyes the color of jade. I am a sucker for redheads.

With Lisa in class, I spent many a time after class stroking my cock to the vision of Lisa, wondering if she was a true redhead, imagining the feel of plunging into her redheaded pussy, until my cock exploded, gushing thick ropes of spunk into a towel. Read more »

[FM] For fun, a male colleague and I agreed to look through each other’s phones. That evening, I masturbated to what I found

This is a guy I’ve known a long time. We had a real laugh in that everybody has certain ‘stuff’ on their phone. The sexual tensions been high for quite a while and we agreed to give each other a 10 minute window with full access to each other’s phones.

The rules were that we couldn’t judge, couldn’t tell anybody else and couldn’t ‘act’/comment on anything.

We sat other sides of the room. I knew full well I had naked stuff, anal beads clips and even sex. On his, I found topless mirror stuff, masturbation stuff and some filthy screenshots from people he’d spoken to/dated.

A huge thrill and we gave each a wink. I’d never tell him, but that night, I masturbated to the dick stuff I’d seen. Particularly an orgasm video, cumming on his mirror.

No regrets, 10/10 fun.

Reconnecting with an old teacher PT. 2 [M22/F50] [Age gap] [Femdom] [Cheating] [Fiction]

The first game of the season went well, our team got the win and we stayed hanging out after the game with other people and got to know some people from the league. I was tired and headed home early, leaving with the thought of how good my teacher looked and that extremely tight hug she gave me as she pressed me against her chest. Our next game wasn’t until the week after so I definitely had to wait a while to see her again, and live with my thoughts for now.

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As we met up before the game the next week, my team and I decided to grab some drinks after as a team bonding activity and to hang out with our new teammates. I debated it, thinking I should head home and just make it a chill night, until all my friends pushed me to come and have some fun. I was hesitant at first as I wasn’t feeling it, but I decided why not maybe some drinks won’t be too bad with my new team. As we arrived to the place I noticed my teacher had came, something I certainly wasn’t expecting as I had thought only the younger crowd would be coming, but hey maybe a chat with her would be nice. I was already fantasizing about her, “this will do” i thought to myself as I walked into the dim bar. Read more »

[MF] I made a new Subby friend!

37m -I found a new Sub friend!

This month has hit me hard. My marriage has completely devolved to a friendship and place to raise my kids. Sex has been nonexistent for a year next week. (My birthday)

Enter a stupid confessions app.
I made a post that I needed to put my hand on someone’s throat and make them mine.

Apparently in my area that’s a good thing because I got a few responses.

One particular stood out. A short, curvy, blonde who really wanted to be dominated. We chatted online for a week or so playing at what we wanted to do. She wants it all.. spanking, choking, cnc, and some more extreme stuff that I may or may not give her cause it pushes even my comfort level.

I wasn’t sure that women like that were really out there and doubted I would ever find one.

We met for the first time over the weekend and it was the absolute best sex of my entire life. Read more »

21[M] Edging as a needy and desperate kissless virgin!

I’m weak and skinny, and absolutely LOVE edging the fuck outta my needy and desperate, 5 inch virgin cock. I’m still really shy when it comes to talking to girls in real life and it’s embarrassing lol. I get hard just from a pretty girl smiling at me and jerk off thinking about what it’d feel to kiss her and touch her body. My cock is just ACHING for a pussy, and I really want it to experience the touch of a woman’s hand. It’s wayy too much used to mine. Sometimes to practice my fucking skills, I just stand on the bed and desperately start fucking the air lol, which is really embarrassing but kinda turns me on. I also like to touch myself thinking about what a girl would react if my 21 year old ass is still a kissless virgin, maybe she’d laugh right at my face? I don’t know lol, but what do you girls think about all of this?

Return to Grace’s End [Fantast] [Mind Control] [Femdom] [Elves] [Edging]

Have something special today. I’ve wanted to work on some fantasy erotica for a while now, and I found this one to be something really special. I hope you guys enjoy reading it as much as I did writing it!

As always, if you want more of my stuff, you can find it at my [r/LibraryOfCaine](https://www.blogger.com/blog/page/edit/412786689543124737/3641746957745797797#) or my blog at [https://libraryofcaine.blogspot.com/](https://www.blogger.com/blog/page/edit/412786689543124737/3641746957745797797#). If you want to find some of my longer stuff like this, consider checking out my [Amazon ](https://www.blogger.com/blog/page/edit/412786689543124737/3641746957745797797#)or [Smashwords ](https://www.blogger.com/blog/page/edit/412786689543124737/3641746957745797797#)pages!

(Final Note, this one was a bit long for Reddit’s post length. So I split it up into the replies.)
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(1/3)
On the southern edge of the Free Lands, where the human kingdoms, fiefdoms, tribes, and city-states jockeyed and schemed and warred for dominance, there was an expansive forest running through deep valleys and jagged mountains that all served as a natural barrier to the unified empire of the elves. At the center of this forest—halfway in, along the singular highway hewn through that rugged land—was Grace’s End, the sole elven settlement to be found in the in the Free Lands. Read more »

[FF] story about me and my long time friend with benefits having fun together~

So for some starting context this story is about me and my friend Lily. We have been close friends since high school during which we on and off dated and near the end of high school we agreed to become friends with benefits and even now in college at 21 years old are both still friends with benefits with each others and some others as well and this story is based of one of the times we got together to have sex about 2 weeks ago ( we have had sec since then but i wanted to share this story since i told it to someone else on reddit and asked if i should post it and they said yes ).

​ Read more »