My Mile High Pegging Fetish Femdom Story

Believe me when I tell you that you have never met a guy that is as obsessed with pegging as I am. If there’s one thing I love, it’s being controlled and dominated while my asshole is subjected to a wide array of punishment bestowed upon me by a beautiful, powerful woman. I have had relationships with various mistresses over the last few years, but none have been quite as fulfilling as my current one. She knows what she wants, and her obsession with putting a big black strapon into my ass is so strong that I can feel fully satisfied with the level of pleasure she provides. My name is Andy, and the woman that I love and cherish – who also happens to dildo fuck me time and time again – is called Alison. Today, I am going to tell you about the most enjoyable pegging experience I have yet to have.

I booked us a holiday to go to Hawaii for two weeks. I rarely get time off work these days, so it was a real pleasure to imagine relaxing by the beach and having a good time with my mistress. When it came to packing, I helped her get everything sorted – as a male slave, that is your job. I put everything where it needed to go, and ensured that all of the sex toys were packed neatly away in our heavy luggage. We got to the airport, checked in without an issue (I always worry that they will see a dildo in the scanner thing and mistake it for something else …) and boarded our flight. We were about five hours in and almost everyone was asleep. With the flight departing at 8 p.m. our time, people were getting some much needed rest and even the flight attendants were pretty docile. Anyway, I was awoken by a hand running up my thigh: what was this?

“I want you to go to the toilet and wait there. Do not lock the door behind you.” – Alison whispered gently into my ear, giving me a kiss on the side of the cheek before returning to her book and making out that she had said nothing.

Naturally, I instigated my movement toward the toilet – what was going to happen? Would I have one of those rare sessions of pleasure that a slave always dreams of getting? Or was I in for some punishment? Upon entering the cubicle, I was amazed by just how small it was. There was barely any room for me, let alone my mistress. Things were going to be awfully cramped.

I waited for what must have been 10 minutes, considering leaving the toilet because my partner had played a trick on me. Just as I was about to open the door, it was slid open and my dominatrix comes in. She has a wild look in her eyes, and I can tell that something is about to happen. Then, out from her top, she pulls out her favorite strapon. I audibly grasped when I realized what it was: how on Earth had she managed to get it into her luggage without me spotting it? The last thing I expected to see in the toilet was that, and I knew exactly what it meant.

I sighed and turned around, unzipping my jeans and letting my ass hit the cold air. I heard my mistress fiddling behind me, presumably to lube up the shaft and prepare it for entry. Then it hit: I just love the feeling, and although it’s somewhat uncomfortable at first, I have such an intense rush whenever my ass is violated by my dominatrix. The fact that we were doing it 30,000 feet above the sea? It made it all the more erotic.

She always starts off shallow, making me think that I have received the entire length of the shaft, but then when I least expect it, she pulls back normally and thrusts extra deep, making me brace up as the full extent of my rear passage is violated. After grabbing ahold of my limp cock, Alison started to stroke as hard as she could. It did not take long for my member to become rock solid – nothing sets my member off quite like being taken like a submissive little whore.

She stroked and stroked as her strapon penetrated me deeper and deeper. I had my eyes closed and in the cold, secluded confines on the airplane toilet, wished that the experience would never end. Unfortunately, my dominatrix had other plans, and soon enough I was being stroked at such a pace that it was impossible for me to control my orgasm. I started to moan quite loudly as the thick blobs of jizz ejaculated from my cock. My femdom mistress took her hand and covered my mouth, making sure that my ability to both breathe and speak was severely limited. I continued to release cum from my cock as it dribbled down her hand. My mistress has always known how to serve her pleasures fully, and the smile on her face that I caught in the reflection was enough evidence to me that she was having a great time.

“Clean yourself up. Also, you have to bring the strapon back. But try to hide it while you walk down the aisle and you will go without orgasms for the entire time we’re here.” – She was deadly serious, and I was worried.

As a final part of my humiliation, I would not only have to clean the whole mess up, but take the tool she used to fuck me back. I felt humiliated, pathetic and submissive – just the way I liked it.

By Dominatrix Draven