I’d explored my fantasies with a transsexual escort several times and after my last encounter, which was the basic girlfriend experience, though she did wear a corset and stockings with satin panties as I asked. She was very open to fantasy play I have long had a scene I’d wanted to play out and she seemed to be the perfect gentle dominant.

Now my thing is dress up. My iconic Mistress isn’t the hard core type. She’s actually quite playful and gentle but she is definitely in charge. My vision is quite detailed. You see, when I used dress my partners as my fantasies I imagine it's me wearing those clothes, wearing the make-up with the lingerie underneath.

As a switch I’m not full fledged CD but I am a bit of a panty-boy when I sub.

So I imagine my fantasy dressed up with a high necked satin blouse. Around her neck is a satin scarf, folded flat with the knot tucked away, almost like a collar, or worn like a cravat with a jeweled stick pin. She has a high-waisted leather wrap skirt or pleated satin skirt on and underneath I dream about a satin or leather corset or waist cincher with either a platform bra or the corset pushing her breasts and nipples up so they rub against the blouse.

Naturally she has FFS stockings cinched to the garters of the corset or waist cincher or a garter belt. A pair of black satin tap pants are pulled over the garters. Kid leather wrist gloves and spike heels round off the look with her hair pushed up and piled. Her make up is dark cherry lipstick with dark smoky eyes and a slash of dark rouge. For perfume, told her I love Chanel 5 or Opium. It reminds me of some pretty hot nights with partners in the past.

I emailed her and she was wiling so I arranged to buy some items in her size to round out her wardrobe and have them delivered directly.

Duly, I presented myself cleaned inside and out. On entering the premises at the agreed time I handed the envelope with the agreed tribute.

Greeting me at the door, she is a vision of my dreams. I did well to outline and source what I fantasized about in terms of clothing and she provided the items already at hand such as stockings and shoes.

So it begins. I hand over the envelope and pour myself some wine and we chat for a bit casually. Then, she stands and moves close to me, rubbing my face into her blouse so I can smell the perfume and get a hint of her hardening.

“Do you like how I’m dressed?”

“Oh yes, mistress, very much.”

“Good. I like it too.”

You walk around the chair to the back of me and then lean in.

“Are you ready?”

“Yes mistress. I am ready.

And so we begin.

“Stand, and take off your clothes.

I do as I am bid until I am naked.

“Turn around and bend over the back of the chair, I’m going to inspect you.”

With that she slipped on a black latex glove and squeezed some lube onto her finger and then rubbed them together. I felt her hand coming up between my legs then a finger as it slipped into my ass. A second finger followed and she twisted them around. Withdrawing them she looked at the fingers she’d inserted and nodded.

“You’ve done well.”

She walked to the side of the room and picked up something and before I knew it she was slipping it in to my ass. I assumed it as steel bung from the cold feel and size.

“There, that will keep you stretched a big while we play.”

Coming to the front she tugged me to my feed and turned me around. Again from the side of the room where there was an assortment of toys and devices, she pulled out something. Pretty soon I saw it was a pink cock cage and she expertly fastened it then went over to my bag and fished around inside.

“These are lovely,” she said, fishing out a pair or pink satin full cut panties with lace around the legs with a small side gusset also in lace.

“Put them on.”

And so I do. She presses against me, her perfume heady and the satin of her blouse sliding against my nipples. I could hear her FFS stockings rustling under her skirt, a supple leather wrap with a high waist which fell to her knees, the flap of the wrap making a slit. She starts to rub my imprisoned cock through the satin panties and I groan as it swells and presses against the cage.

“So you like to wear satin panties,” she smiles. “Tell me more.”

I do indeed have a long history of stealing panties and lingerie and dressing up, though I have never gone the full monty. I begin to explain. It was mostly the naughtiness of taking the items from my mother and stimulating myself which drove me since I was about sixteen. I have worn panties and some lingerie in role play with my partners but rarely. I have also been sucked or jacked off with a pair of silky satiny panties.

I do love the sensual rustle of nylons, the slip of satin and the scent of leather and over the years I used to pick out clothes for my partners and have them dress up as my fantasy.

I have dabbled with BDSM, role play, dress up, both as a top and a bottom. And after sampling a wide range of options, I’ve come to the conclusion that dress up is what I crave.

Sometimes I would bathe and dress her, playing the role of a submissive servant, talking about how Master or the client will be pleased. On the rare occasions I bottomed, I would also play the submissive servant, preparing her for a client who would soon arriving. In dressing her as a domme, of course, I indulge my own fantasy of what she will look like.

Recently my fetish life has come to a halt. My current partner has hit menopause and lost all interest in sex. So I indulge myself and I have been on a quest to find one or two escorts who will fulfill my suppressed fantasies.

“So why do you think it’s attractive to you? Why act it out?”

“Being moderately feminized and humiliated is a turn on because it confronts my fantasies and past behaviour. It forces me to confront my deepest fantasies and besides I get really turned on by the satin and silk, they are just so sensual against my skin,” I answer. “Lately too, I’ve found myself coming back to she male sites, especially the high quality one like TS seduction.

She bids me stand and rubs her body against me again, he hands pressing more on my cock.

“Come here and bend over,” she says, and I do.

My panties are pulled down to expose my ass and she steps to the side rubs my cheeks gently.

“Well, I have to punish you for violating those womens’ privacy, that wearing women’s clothing is not wrong but special and you should think enough of myself to acquire my own collection.”

Of course, that would remove some of the thrill, but I get her point.

The spanking begins and I writhe. With each stroke she pauses and asks me to list the women whose lingerie I have pawed through, and used to gratify myself..

“My mother”

Smack

“My aunt”

Smack

“The next door neighbours.”

I go through the list, confessing to liking women’s clothing and cross dressing starting as a teenager.

Any woman I stayed with would become a target for my explorations. Mostly, I craved satin-nylon material, they were soft and erotic against my balls and cock. I was still small enough at this age to try on their stockings and garter belts. My mother had a pair of white nylon sanitary panties with a vinyl gusset which I discovered early in my adventure and I was completely taken.

She stops and leaves me bending over. She releases the steel bung and quickly slips in a slightly larger one. My panties are pulled up and she steps into kiss me fully on the lips.

“Very good,” she says.

She unbuttons her blouse and casts it off, revealing a black leather under-bust corset with thick erect nipples. She pulls me closer, directing me to her breasts and I begin to eagerly lick and suck on her nipples which harden at my ministrations.

"What else have you explored, in terms of cross dressing?"

“Not much more, just panties and slips, though sometime I have put on stockings with a garter belt, Mistress,” I say.

She asks: “Have you told anyone. Share these desires experiences with anyone? Ever sucked a cock? Been fucked in the ass? With a cock, a dildo?"

I murmur my responses. She smacks me and demands I speak loudly and clearly.

“Yes, I have explored TS encounters with escorts,” I respond.

She slips off the satin scarf from her neck and unfurls it, rubbing it across my face and body, paying special attention to my cock which is begging for attention. Of course I just get harder.

Taking her skirt off she sits down in a chair and bids me to come forward and kneel, which, of course, I do. Pushing my face into silken crotch I do what comes naturally, licking and blowing hot breath through the panties to excite what lies below. I feel it stiffen and grow and when I have served enough, she decides it’s time to take me. She makes me kneel on the day bed and slips out the bung. The scarf has fallen into my hands and I grateful caress myself though the panties.

She reaches down to free my cock from the confines of the cage and its not long before I’m rock hard. Her cock pushes into me and starts. It’s painful at first but soon her cock is gliding smoothly and I am feeling ripples of pleasure from my prostate.

Suddenly she pulls out and whip off the condom and moves around to my mouth, where she slides her cock in and comes, a sweet salty torrent. It’s enough to trigger my own orgasm and I start to come as well, splattering over the scarf and panties.

It was an expensive experience at $400 for her time plus $200 for lingerie and clothing, but one I will always remember and may indulge in again.

On the other hand, I’m thinking of asking her to dress as a submissive sissy satin maid so I can top her.