Author: maniacalenjoyment

10+ men jerking off to me having sex on a stage in Portland (M/F)

Traveling for work was never the romantic and exciting endeavor I imagined. What it really comes down to is you’re doing the same work, usually more of it in a place that is typically not comfortable. I learned real quick that because of this I would indulge as much as possible. I spent as much money as possible using any trick I could to eat well and live well. I also indulged sexually where I could and had some great experiences everywhere I’ve been.

One time I was in Portland and wow did I fall for that city. I have no idea how I came across it but heard about an adult theater. I had never been to one and just imagined them to be grimy but was very horny. So I just went. I admit, even with all my experience and confidence that I can still be quite nervous when trying new things. My heart was racing, my mind was telling me to just turn back and the only thing I could do was tell myself I could turn around at any point. I walked to this place from my hotel and noticed it was just like a video store. Read more »

First threesome (M/M/F)

Its interesting to see what you can remember so vividly after so many years. My first threesome was one of those situations. I was 21 and I had just gotten off work late at night and got onto my computer to see if any of my friends were around to meet up. Back then I used AIM and Yahoo as my main chat programs (before they became creepy or spam filled) and received a random message from someone. On yahoo you used to be able to list some details ( like age and sex and location) and people could find you that way.

So the message was from the guy part of a couple who said they were older and looking for young guys. The guy loved to see his wife fuck other men and would join in. I honestly didn’t know what to think. I’ve never even thought of the possibility of this and it was all new to me. They sent me pictures and I was very turned on by her. I told them I would do it but was about to cancel. I decided to jerk off instead thinking that once I had this moment out of my system I could get just move on and forget about it. I jumped in the shower afterwards and I was just nervous. Everything in me screamed that I wanted to do this but I was almost shaking at the thought of it. Read more »

A sexy massage (M/F)

I was asked by two different folks to be more descriptive about the sex versus the situation. I actually enjoy the setup and expressing the thoughts that went through my mind but I will provide more sex details.

So this is probably one of many stories with my friend/lover Ashley. Up until she moved two years ago we had a rocky, passion filled relationship which to this day I still can’t figure out why. She is a beautiful woman with a unique ethnic background of European and Polynesian descent. At 5’3 she has beautiful dark curly hair, big enchanting hazel eyes, a few freckles and creamy soft skin. Her breasts, god her breasts were beautiful and a plump C with medium sized nipples that loved to be punished. She has birthing hips and sexy thighs and tattoos all around her body.

Ashley was the complete opposite of me. She was the laidback hippie, always wanting to make the world better and a deeply emotional person. She pulled me through some difficult times by giving me a place of mental refuge when I needed it most just by being the person she was. Our first dates ended horribly with our strong personalities clashing and yet we were very attracted to each other. It eventually led to a friends with benefit type situation because we couldn’t stand the idea of dating one another in the initial stages. Read more »

A submissive squirter (M/F)

This story goes a few years back with an older woman I met online. I admit she is one of the few people I never "got" and to this day I can only speculate what the scene was about. I had just moved to North Carolina and was having a hard time with my new sexual lull. Back home I had a good number of friends or places I could frequent for lovers but in NC I was drawing blanks. My charm and looks just didn't fly down here so I started to date and seek lovers online.

I met Stacey (not her real name) through okcupid or craigslist. She was 15 years older than me, had beautiful curly red hair, creamy skin and a body that showed her careful devotion to yoga and healthy eating. Like me she was from the northeast and had a powerful laugh that paid no attention to anyone around her. I took her to dinner and thoroughly enjoyed her company. Quite honestly I thought I was going nowhere but it turns out I used a few choice words with her that raised her eyebrows and shifted me over to potential lover status. In my joking ways I talked about spanking her for some sarcastic comment she made which she seemed to love. Read more »

A new experience with a Sugar baby [35M/24F]

The idea behind a sugar relationship was always unattractive to me. It wasn't the concept of taking care of someone financially so that they sleep with you because I'm comfortable taking care of others and have slept with prostitutes on occasion. It was the grey ground of not knowing what it really was. With a hooker you know exactly whats happening and you have no qualms that what is about to happen is just because you're horny and that person is going to satisfy you. With a regular partner, you have a chance to date and develop feelings. But with a sugar baby….it's almost all fake. There is no genuineness there that doesn't exceed the financial value that you give them. It's a total farce.

With that said, I still decided to give it a try. The other thing that was odd about it for me is that I'm actually a pretty good looking guy. I did it because I was honestly bored and wanted to see who would come my way. So enter this 24 year old beautiful European goddess with a 5'9 frame swelling with large breasts, tight features, and great hips. She is actually very smart, holds a great conversation and is passionate which I like. After a while of chatting we finally got together. Read more »

Enjoying a thick guy in NC (m/m)

I detest titles but I guess the best term to describe me is bi-sexual, though frankly I have zero attraction to guys. It's a purely sexual endeavor that I crave from time to time. I've slept with women, men, cross dressers, MtF, and FtM's. I'm either a very curious person or just ridiculously horny.

I've written here before but deleted the stories once I realized it could be traced back to me. I'll be more careful this time especially since I share a side of me that no one knows. A few years ago I moved to NC and put out an ad on CL for a guy. I was seeking to bottom, something I rarely ever did to that point. The thought of it is scary more because of the pain aspect. Up until that point every single encounter but one was a painful procedure that left me only wanting to top guys. I still had this urge. Many guys replied. I was one of the few actual young guys seeking someone older. I figured an older guy could be more gentle. Read more »