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when Melissa slid the strapon dildo into my virgin ass. I almost came on the spot, but there was so much more to come.
We had known each other many years, and have developed a very close relationship. We had been there for each other in the good and the bad times, and it was really a great friendship that had blossomed into 'with benefits' over time. She was a firecracker in a great small package: 5 foot 5, 130lbs, shoulder length brown hair, nice 34Bs, wide hips, and sparkling eyes. A lot of guys looked at her and saw MILF, but little did they know really how deep those waters ran. They also saw "woman", but didn't know the dominant streak that ran through her.
We had been delving into some deep conversations about gender roles and power exchange over lunch one day, and the topic turned to turnabout, female to male. I had introduced her to the idea of "pegging", and she was intrigued. She even got me to blush as I related that it was a secret fantasy of mine to be pegged by a dominant woman. As it turns out, I found the right person in the world to tell that to, and the wheels were set in motion.
Having finished the business I had to travel for, I was preparing to travel back home the next day. I had finished up the business I was there for early, and I had a free night to kill before flying the next day. I had thought to pack my running gear, and went for a nice long 10 mile run around the hotel, and had made it back to my room after a good sweat and into the shower.
It was almost eerie that as I exited the shower, there as a knock at the door. Not being shy, I wrapped myself in a towel and looked out the peephole to see Melissa standing there. I fumbled as I opened the door as quickly as I could, swinging it open to see my awesome friend standing there.
"Hey!" I said with surprise, "what are you doing here?"
The answer came in the form of a hand to the chest, pushing me back inside the room, her eyes locked on mine, automatically closing and locking the door as she passed it. That hand kept pushing me back into the room until i got to the king bed, and it pushed me down onto the edge.
"I'm here to do you." she said, smouldering in the delivery. "I couldn't get the last conversation out of my head, and the stars aligned."
She was explaining this as she placed her suitcase onto the dresser and unzipped it. Her coat came off, followed by her blouse and skirt, revealing a corset and garters/stockings combo. She quickly swapped out her 2" heels for 4" heels, and turned to face me. I was having trouble in keeping my cock under control, but it wasn't the first time we'd done this kind of thing, and I was fairly sure that I was going to end up having sex with Melissa today.
Then the surprise happened. She reached into the suitcase and produced a harness and a very interesting dildo. she strapped on the harness, inserted the dildo into the harness and her end into her, and stood there, a picture of dominant femininity, fake cock sticking out in front of her.
"Suck." she commanded. "And naked."
I assented with a quiet "Yes, Ma'am", and stood to drop my towel, and then knelt to begin servicing her cock. I concentrated on my task, discovering that I could take the 7" cock in my mouth and throat, and focused on making sure that I was doing as much as I could to pleasure her through the dildo connected to what was in her pussy.
After 10 minutes of her groaning and grinding her hips into my face, she pulled my hair back to stare into my eyes, and breathed "It's time."
I knelt on the ottoman at the end of the bed, and parted my knees. She reached back into the suitcase and produced a bottle of lube, which she proceeded to use to lube up my ass and the dildo in her harness.
She stood behind me, admiring the view. She stroked my hard cock and dandled my heavy balls, and teased my asshole, before I felt the pressure of the fake cock against my ring. I was fresh from the shower, so it wasn't a big stretch (ha!) and before i knew it, she was clit deep in me, the dildo completely encased in my ass.
I heard an impressed, low "fuck" from her; Melissa was totally getting off on this. She started to fuck me, and I fucked her back, feeling my anus stretch as she pounded me, and my cock and balls swinging free. she smacked my asschecks, reached around and squeezed my cock and told me in no uncertain terms that I would not come until she said so.
I can't tell you how long it was that she fucked me, but I do recall her having me flip over so she could blow me at the same time as she fucked my ass. She had six or seven orgasms, and finally unmounted me. I was driven wild by the whole experience: her, the assfucking, the dominance. She composed herself, and offered me a trade: she would blow me and let me cum if I cleaned up her dildo that had just been in my ass.
If my cock could have gotten harder, it would have. that was about the nastiest thing I'd ever done, and I did it: sucking the ass taste off of her fake dick delivered her one more orgasm. She unstrapped, and then expertly blew me until I unloaded all over her face (a particular fetish of hers), and we napped together until hunger awoke us. I wonder what dinner conversation would lead us to - I still had 12 hours to go before I had to fly out!
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Categories: Oral Sex, Steady Partner, Identified partner, The Fetishists, Anal Sex, S-M / Domination / submissive
Location: A hotel room | Roleplay: Any
Fulfillment: Share it only | Nature: Agressive