Author: DppThrow999

[MF] My second visit with Emily Part 1 [GFD] [Femdom] [AgeGap] [Strap-On]

> “11am at my place. Would you be interested in trying a few things with me?”

Sadly I couldn’t make it as I had to work. So, it ended up being the following Saturday. I made damn sure I didn’t work that day or the day after. Emily understood, but part of me felt like I was letting her down. Yet we kept texting like all new young lovers do.

Emily was a woman who knew what she wanted, and how to get it. I had no idea what those “few things” she wanted to try with me were. All I knew was if it was anything like last time I’d probably be okay with it. Thursday came around and I got another text from Emily. We had been flirting with each other throughout the week a bit. Yet this text was a bit different.

> I got a new toy for you! I’ll show you when you get here! Read more »

[MF] First time getting pegged [GFD] [Femdom] [AgeGap] [Pegging]

In my previous story I mentioned how I had an itch inside me which did not need to be scratched, but *wanted* to be scratched badly. However, my path to BDSM was not a straight line. First, I figured if I were to do anything anal again I’d want it to be with a woman. Second, I was apprehensive about looking for older men I didn’t know to scratch that itch. So, the best option I could find was finding a woman to peg me.

My search started by finding **MANY** Femdom personals. All of which required payment, and all of which seemed like a business transaction. No connection. No heart. This was *not* what I was looking for. With this I took the plunge, made an email specifically for this able to be nuked if this didn’t work out, and made a personals ad on CraigsList, way back when it was easy to do this.

The ad was pretty straightforward: “22 M Curious about being pegged”, and in it I laid out my preferences and limits. Essentially I was looking for someone 40 and under, who could host, and was comfortable with a first timer and not jumping into things. I did specify I wasn’t looking to pay for anything as well. Hitting “Post” made me realize I was holding my breath, and was far more nervous than I fully understood. Read more »

[MF] The time my keyholder pushed my limits [Femdom] [Bondage] [Sharing] [Pegging]

**PART 1: Prologue**

**PART 2: The Experience**

In my early 20’s I was VERY adventurous with my sexuality. I had a nearly year long fling with a man 10+ years older than me, but it ended when he moved away. Somehow this left a void inside me. An itch that did not need to be scratched, but *wanted* to be scratched **badly**. This is how I stepped into the world of BDSM, met some amazing people, had many experiences I remember fondly even now.

**PART 1: Prologue**

A little under a year after my fling I was still unsure if I was Bi or just Bi-curious. Having been going to a BDSM munch for a few months and this was where I met my future keyholder. This was a surprise to me as I did not have a thought in my mind I would be the bottom/submissive. Yet somehow, we will call her Heather, had won me over.

Heather was a powerhouse of a person. 37, 5’3″, curvy MILF with kids in college, Divorced, and was often assumed to still be in her 20s. Her personality was witty, intelligent, and funny. She had a way of putting you at ease while she got what she want, and you somehow got what you needed. This was how I found myself locked in chastity by her. Read more »