Author: insecurepup

I [f] had a threesome with two [m]ale co-workers

I work at a techie startup that is predominantly male. New policy has me going into the office twice a week.

More recently, the company had its first happy hour in a while. We went to a local bar and it was a professional enough setting until everyone left except me and 2 co-workers – let’s call them Marc and Jon. We were all pretty drunk and decided to go dancing at a nearby club (we’ve all been vaccinated and wore our masks).

Marc and Jon don’t work directly on my team but I’ve worked with them a bit and have always been super friendly. I’m a petite girl with perky breasts that are a perfect handful and a little round ass. This night I was wearing a form fitting cropped t-shirt that hugged my curves and a pair of soft wide leg pants – it was a simple work appropriate yet comfortable outfit that I felt confident in. Read more »

Getting creampied [f] everyday by my married boss [m]

At my last company, my boss and I developed something more than a working relationship. Our roles were very collaborative and I would often be in his office for brainstorming and feedback sessions. From the beginning, I could already tell he was attracted to me by how closely he would come up to me when talking to me and by his body language around me. That being said, I also knew he was married, so I tried to avoid thinking about him in that way.

On one particular day after I’d been working at the company for about 4 months, we were in a meeting together and it was getting late. My boss asked me if I wanted to continue our discussion over dinner – his treat. I agreed to it, not thinking much of it.

He took me to a sushi restaurant that was a bit more upscale than what I expected. Instead of discussing work matters, he began asking me personal questions about myself, my relationships, my view on love. While this might’ve raised red flags for me if I weren’t interested in him, I can’t deny that he was an attractive older man and his line of questioning didn’t bother me. He was in his 50s and about 6’2” with mesmerizing blue eyes and a full head of silver hair. Not to mention he was successful, obviously fit, and intelligent. I admittedly had a small crush on him, and maybe he could sense that. Read more »

How I [f] got trained into being a submissive fuckhole

Whenever I go to bed with a man, he always seems to ravage my body in the roughest manner possible. It started when I was just 18 with the first guy I ever slept with.

Zach transferred to our high school during senior year and all the girls were infatuated with him because he was tall, dark, and handsome. Classic trifecta. Little did they know he had quite a big cock as well.

He took a liking to me in class and the other girls were jealous. At the time however, I had a boyfriend, Sean, but Zach didn’t seem to mind. Sean was saving himself for marriage and I was a very horny teenager. Fast forward a bit and I found myself having lunch with Zach. Lunch soon turned into hanging out with him over the weekend while Sean was at work. At first, our hangouts were innocent enough, but the sexual tension was undeniable. Finally, on one occasion, we were sitting on his bed watching a movie when Zach slowly began to stroke my thigh. When I didn’t resist, he moved on to finger me. I was still a virgin at the time and he made me cum from his finger alone. I could never admit to myself that at that moment, I had cheated on Sean. Read more »