In my line of work, I help people. Most of them are regular every day people who get caught up in something and are looking to make it stop or a way out. Some are high profile politicians, business people, entertainers, and celebrities. One of my clients, however, is a professional dominatrix.

Recently, I helped out her out of a situation with an unhappy wife who discovered her husband had been using her services. The wife was threatening to go public with the location and to name names, which of course was bad for business since her clients demanded utmost discretion.

I made it all go away, and for that she was grateful. We’d set up a meeting at one of her apartments for me to deliver the final paperwork and for her, of course, to pay me. As it turned out, on that day, she was called out of town on business, which was a shame because I always liked spending time with her and sharing stories.

She insisted I still go to her apartment; she would have one of her people there to give me a cheque and to receive the paperwork. When I arrived at the midtown high rise condo, however, there was a surprise waiting for me. Greeting me at the door was a young submissive, clearly one of Mistress D’s slaves.

She smiled shyly and bid me enter. Before I could say anything, she said, “Mistress sent me here, I am to give you two envelopes, and you are to give me one envelope.”

Indeed, she furnished two envelopes and handed them to me just as I passed on my package. One, clearly, was full of cash. I didn’t bother to count it but slipped it into the inside pocket of my suit jacket. I opened the other to find a handwritten note:

This is Vicky. She is one of my sissy submissives. She has been told to prepare herself specifically for this afternoon according to my instructions. She is yours to play with as long as you want. All I ask is that you send her home the way you found her!!
Enjoy! You have done me a great service.

Inside the envelope was a small key which didn’t immediately ring any bells. Still, this could be interesting I thought as I walked over to the couch and sat down.

Vicky was dressed very conservatively in a silver satin blouse, seamed stockings, white strappy heels and a layered chiffon skirt with sunflowers which came to her knees. She was very attractive with her brown hair neatly trimmed and set and soft pastel makeup.

“Vicky, go open a bottle of wine, I’m sure there’s a chilled chardonnay in the fridge, pour me a glass and bring it here would you?”

I took a sip of the wine and leaned back into the couch.

“So Vicky, spin around here let me get a look at you.”

Vicky was immediately responsive. Good girl. She’s clearly been well trained.

“Now, lift up the front of your skirt and pull down your panties for me.”

She did as she was told and I saw a  six strap white garter belt attached to seamed beige FFS stockings. She was wearing pink and white satin French cut panties, and as she pulled them down, I could see she was in a cock cage, the kind which has a series of rings that restrict the erection but leave the head exposed.

“Very nice. Now turn around, pull up your skirt at the back and leave your panties down.”

Again, there was no hesitation. She bent over to reveal a jeweled princess butt plug, securely fitted into her ass.

I told her to pull her panties up as I got up and took a walk around the condo. Mistress D didn’t live here, but she did entertain clients, mostly for feminization I would guess, given the big makeup table, the wall of wigs, and the dresses, skirts, and blouses on wheeled hanger racks. There were several full-length mirrors set up so if you stood in the middle of them you could see every angle of yourself. There were a few bondage stations too, and, hanging from a series of hooks a collection of whips, paddles, floggers, and crops. Next to them were some restraints. Also, there was a shelving unit with various sized butt plugs, dildos and lubes.

 I went back to the living room area where Vicky was waiting for further instruction. I came around the back of her and leaned into her neck. 

“So, Vicky, are you ready to serve me this afternoon as directed by your Mistress?”

“Yes, sir. Always.”

‘Good, let’s get this party started.” 

I reached around for her breasts and felt her nipples harden as I played with them. I pulled her blouse apart, leaned in and started sucking on them until she was moaning with pleasure.

I put down my wine glass and motioned for Vicky to drop to her knees as I unbuckled my pants and dropped them to the floor. I stretched out my cock from the confines of my underwear, which I also dropped, and offered it to her eager lips.

As she went at my cock to wake it from its slumbers, I took off my shirt, then socks and shoes. It didn’t take long for me to get going and soon I had a full on erection.

“Okay Vicky,” I said, moving to sit down on one of the single high back chairs. “Over by the wall unit you’ll find some latex gloves and lube. Bring them over."

I stroked my cock as she brought back the items to keep it hard.

“Now, put one glove on your right hand, lube it and then kneel down between my legs,” I instructed her. “I want you to give me a prostate massage while you also give me a blow job. Can you do that?”

She nodded and gently inserted her index finger into my ass. It was well lubed and slipped in easily as she turned it upwards to seek out my prostate. Good girl. She found it on the first try and began to softly rub it while bobbing up and down on my cock.

It was heaven, but I was determined not to come this way and not this quickly. I let her go for a few minutes until I felt I was going to come and pulled back.

"Okay," I said, "let’s get you into the party as well, you’ve been very good."

I pulled her up and lifted her skirt to expose her panties and the cock cage. Taking the key I found in the envelope, I released her from the device and set it aside.

Next, I reached over to the butt plugs and grabbed a larger one than the princess plug I had just pulled out, lubed it and slipped it in.

“There,” I said rubbing her stiffening clitty in its cage through the satin sissy panties. “That will get you stretched out for later and meanwhile you can have some fun.”

I turned my attention to her breasts and nipples and toyed with then through the satin blouse, occasionally slipping my hand under the fabric for a direct caress.

I reached under her skirt and rubbed her clitty through her panties. It was getting harder by the minute now that it was free to grow. After an interlude of caressing each other, I directed her to the high back chair where I had her kneel on it facing backward.

Slipping on a condom, I pulled out the bung and added some more lube before pressing my cock head against her little rosebud. I didn't even bother taking her frilly panties off, just pulled the gusset aside.

I slipped in easily. Being well lubed, I soon got a good rhythm going, and she began to buck and moan as she jerked away at her clitty.

Things were building to a head, so I took her over to the daybed and had her lie face up and entered her again. She continued to jerk herself off. I wasn’t going to stand on ceremony and demand she ask permission to come.

“If you want to come, just come,” I said. “I’m pretty close.”

With that she moaned louder and thrust against me, squeezing the head of my cock tighter on the backstroke and relaxing as I pushed in.

When I felt that familiar explosion building up, I decided on a whim to come on her. Just as I pulled out and tugged off the condom, she came too, great gobs of cum gushed out and onto her panties and belly, some getting on the inside of her skirt. I followed spewing a stream of cum over her pretty dress and panties.

When we’d recovered, I sipped on my wine while she cleaned up as best she could.

“If Mistress wants to punish you for making a mess tell her I told you to come on yourself like that,” I said. “And of course, I came all over you too!”

“Oh, thank you, sir, that will be a help,” she said.

I finished my glass, dressed and left her to clean up.