I had been fantasizing about having sex with a Dominatrix for several years. I was now in my early fifties, divorced, and wanted to explore a few of my sexual bucket list items.
Two years prior, a short-term “friend with benefits” woman introduced me to ass play. Rimming, eating ass, toys, and prostate massage. I loved it all. And, oh my god, the orgasms I had from most of the prostate massages were intense full-body experiences. She had used her toys on me, and we even discussed getting a strap-on to try pegging, but we never did.
The pegging discussion led me to watch a lot of pegging videos on Pornhub. Most were simple husband and wife couples, but a few were women dressed in sexy black leather or spandex outfits, complete with high heels, a few with masks, and of course, strap-on cocks.
I was not into the whole stereotypical BDSM “whips and chains” type of stuff, but I had the fantasy that if I was going to be ass fucked and milked with a strap-on, a hot, sexy Dominatrix sounded like an exciting sexual experience.
About the same time as my FWB, another divorced guy mentioned to me several websites where he was meeting “professional” women for sexual encounters. Yes, prostitutes. Today they go by the term “providers,” and the men are known as “hobbyists.” I guess these are the politically correct terms for hookers and johns in today’s progressive world.
After scanning the websites for several weeks, I finally found one woman who really interested me. First, there are few women who offer pegging. Second, most are very Dom-oriented. Third, most are not very sexy as they tend to be overweight butch dyke women.
I finally found one who was more provider than Dominatrix, but she offered pegging. Her ad listing had a photo of herself in a sexy outfit wearing her strap-on. While she offered “full service” she knew there was a market for regular guys who wanted to be pegged. She was Mistress Lisa. She was a small BBW, a curvy size eight-ten, five-eight in height, with large 38DD breasts, and long straight black hair.
In her photo, she wore a black fishnet bodysuit with cutouts for both breasts and a crotchless section. She added a black leather crisscross kind of vest, with one-inch-wide straps and faux diamond studs, a matching leather strap-on harness, and black thigh-high shiny boots. She was sexy as fuck. Her client reviews were all five stars and her rates, or “donations,” were reasonable at $350 per hour. Lisa also had photos of her various toys, butt plugs, nipple clamps, floggers, etc.
I sent Mistress Lisa a text with the required information that was listed in her website ad. A couple of hours later I received a reply asking me to call her back at a specific time that evening. My cock twitched with anticipation.
That night I called at the designated time and a sexy woman’s voice answered, “Hello, is this Paul?”
“Yes. Hi Lisa,” I said.
In a stern voice, “You will call me Mistress Lisa at all times.”
“Yes, Mistress Lisa,” I replied.
“Good,” she said. We spent the next ten minutes going over what I was interested in, my experience, and such. We booked a date and time, and I was given instructions on what to do that day.
Two days later I pulled into the strip mall parking lot per her directions and texted her at 2:45 pm. I received a text back with her nearby address and was told to text when I parked, but not to come to the front door.
Soon I was pulling up at her private residence. It was a nice quiet neighborhood and her home had great curb appeal with a well-maintained lawn, pruned shrubs in the flower beds, and there were a lot of potted flowers on her porch. I texted again. I could see a dark figure look out from what I believed to be the kitchen sink window. Her text read, “You may come to the door now.”
I was a bit nervous as I walked up the brick pathway. Right before I could knock on the door it opened. “Come in, Paul.”
The foyer and living room were a bit dark. As my eyes adjusted, I laid my eyes on Mistress Lisa. I first noticed that she was dressed in the same sexy outfit in her ad photos. Then I noticed her pretty face and flawless makeup.
“Hello, Mistress Lisa,” I said.
We sat down in the living room and chatted briefly as we reviewed my expectations for the session. Mistress Lisa explained that she would have me get undressed, and then start me with a simple butt plug while she started with a short massage of my ass to relax.
I followed her back to her “playroom,” as she called it. As I entered, I stopped dead in my tracks so I could take it all in. The walls were fire engine red with black painted trim around the windows, closet, and door. It also had one horizontal stripe around the room, about waist high, and about one foot in width. The room was filled with a large chair, a bench, a swing, and several other items I could not name. On one wall hung a variety of items: handcuffs, paddles, whips, floggers, and such. There was a small table that had a variety of anal toys in all sizes, shapes, and colors. Everything was very well organized.
“Well, what do you think?” she asked.
Laughing a bit I told her, “All very interesting. But nothing here surprises me.”
She directed me to undress and to lay down on the bench face down, ass up. The bench was about three feet wide and six feet in length. The frame was four-inch tube steel that was painted black and the padded bench was red. It had several “arms” off to the sides, and a few that went up several feet. It reminded me of an octopus as it had so many items coming off of the main bench.
Mistress Lisa told me, “I’m going to lube up your ass and start you off with a butt plug.”
As she was applying the lube to my ass, she also coated my cock and balls.
“You have a nice cock, Paul. I bet the ladies like you.”
I was flattered. I’m sure she’d seen hundreds of cocks. I had good genes as my father and older brother had big cocks, and I was six inches soft, and almost nine inches when hard. I was almost seven inches in girth when erect.
Mistress Lisa slowly guided a stainless steel butt plug into my ass. She excused herself and said she would return shortly. About ten minutes later, there was a knock at the door. I looked up to see Mistress Lisa standing in the doorway. She had her legs spread wide and her hands up touching the corners of the doorway. She looked stunning in her sexy Dom outfit. My cock twitched.
“Your hour starts now,” she said.
She came and sat on the end of the bench and slowly removed the butt plug. She reached over and grabbed another, but larger. She applied lube and slowly slid it into my ass. “I will now get you into position. I’m going to tie your wrists to the outer posts and your ankles to the upper posts. This will get you in the best position for the pegging and prostate milking.”
Mistress Lisa opened a drawer and pulled out several pieces of long red rope. She tied my ankles first, and then my wrists. I was now at her mercy with my legs held high in the air and my arms extended out to my sides.
“Paul, you’re a handsome man. Let’s get your cock hard to start things off,” she said with a smile. She sat back down on the bench and started to fondle my dick and balls. Soon she was stroking me. “My, what a nice big cock.” She leaned over and licked the entire length and then swirled her tongue around my large mushroom head.
“Damn that feels great, Lisa,” I whispered.
She squeezed my dick hard, “You will only call me Mistress Lisa. Is that clear?”
“Yes, Mistress Lisa,” I said.
Laughing, she said, “I’m really into your big cock.” She again licked my shaft and then took half of it into her mouth and give it a few bobs up and down as she stroked the bottom half.
“Mistress Lisa, you are such a tease!” I said.
“I’ll be honest. I don’t usually give blowjobs, especially to first-time clients. But your cock is making me horny,” she said with a giggle. She released my cock and began rubbing her pussy.
