Chance Encounter

Chance encounter

I was sitting in a local coffee shop enjoying my coffee and muffin when an older, about my age man approached my table and asked if he might sit with me. Glad for the company, I said sure and to my surprise, rather than sit opposite me, he slid next to me on the bench seat.

"I noticed you sitting all alone and thought that you might need some cheering up." He said. I was a little nervous, but curious. "Thanks", I said, there has been a lot I have been coming to grips with recently." Wow -- why did I tell him that.

"What kinds of things?"

"Although I am 70 years old I have been discovering a side of me that had been pretty much hidden most of my life. " There that wasn't to revealing.

"Are you questioning your sexual identity", he asked seemingly from out of the blue?

"Why do you ask that, I stammered" because in fact he was spot on. To say I have been in the closet for most of my life is an understatement. As a young man, I did have some brief gay encounters, but I locked myself into the hetero role that was prescribed by my family. There was no room for exploration.

"I noticed that as you scanned the room, you seemed to be attracted to the women's clothing and in particular their shoes."

"You make that sound as If I have a fetish."

"No -- not at all. I was just making an observation."

As an aside, I should note that I have been attracted to women's wear as long as I can remember, but kept it buried for the most part. I felt ashamed and could not see an outlet for that urge in any of my relationships.

"That must be hard for you," he said, as I felt his hand rest on my thigh. My first impulse was to bolt, but his hand was both soothing and arousing. I looked into his kind blue eyes and felt an attraction that was new to me.

"I think I can help you with your problem if you will let me."

"What do you mean, I asked."

A his hand slowly brushed my thigh, I found myself getting more aroused.

"I would like to help you explore your boundaries. Would you like me to be your guide?"

Surprisingly, I said yes. "When would we start."

"Now!" as he brushed over my hardening cock.

"First, you must agree to do whatever I tell you when I tell you."

"If you do, I will help you be the gurl you were always meant to be."

"What do you say -- are you "up" for this."

"I'm not sure, but I guess so."

"OK -- take your hand and caress my thigh just as I did yours."

I brushed my hand across his thigh and that felt naughty (?) and wonderful.

"Now trace the outline of my cock with your finger and feel it growing."

I felt his penis grow under the ministrations of my fingers.

He turned my face towards his and briefly kissed me with a smile.

"Let's go someplace more private."

"By the way my name is Roy and now your name is Toya."

As we left the café, Roy helped me on with my jacket -- what a gentleman.

He suggested we go back to his place.

I followed in my car back to his home in a nice neighborhood.

He had me park my car in his garage.

I helped Roy make some snacks and we settled down in front of his large screen TV.

"Toya -- I am going to show you some videos that I find quite appealing and I hope you will too." He keyed into one of the porn sites and searched for "Gay Crossdressers, Sissies, Feminization." I have to admit I have fantasized about crossdressing and more.

"Do you like this," asked Roy. "Yes", I squealed(?) -- where did that come from?

As we watched the video, Roy took my hand and guided it to his belt. I took the hint and began to open his trousers. I was a bit surprised when noticed the lace panties that Roy was wearing. After a bit he stood up and took off his trousers revealing his black garter belt and thigh high lace stockings. He looked amazing.

"Toya are you ready for your first lesson?"

"Yes Roy," I replied. "My name is Rhonda Toya and I am a lot like you."

"Do you like what you see."

"Yes!"

"Would you like to dress like this?"

"Yes, I think I would."

"Are you ready to give your first blowjob?"

"Ahh...what?"

"Remember you agreed to do whatever I asked in order that I may help you."

He had me kneel in front of him as he sat on the couch.

I took my hand and traced the outline of his growing cock.

As I pulled down his lace panties, he sprang to life. I brought my lips to the tip and gave it a little kiss. I ran my tongue around the tip and took him into my mouth.

Slowly, at first, I bobbed up and down on his cock enjoying the taste and the feel. I found I could take his 6" cock in almost completely. He took my head and had my lips feeling his balls slap against them.

"Go ahead Toya take it all in," he said and I did. He guided my hand to his anus and he told me to gently rub it which I did. I must have been doing something right as he soon shot strings of white cream into my mouth. I had to swallow some, but saved some to show him just like they do in the literotica stories. I looked at him, blew some cum bubbles and then swallowed it all.

"Good job, Toya, I think you will make a great sissy cocksucker."

Still in a daze he led me to the bathroom. There I was instructed to take off all my clothes and set them outside the door before showering and shaving.

"Make sure you shave all over." You don't want to have any body hair except eyebrows and on top. After shaving apply this depilatory cream."

When I came out of the bathroom, I noticed two things, my clothes were gone and that there was a beautiful ginger haired woman staring at my nude body.

"Don't be nervous Toya it's me," said Rhonda "I am here to help you," she said as she led me to a room that was frilly and feminine. I really liked it.

"Let's get you dressed before you catch cold."

Rhonda sat me on the bed and handed me a pair of pink thigh highs.

As I rolled them up my leg, I noticed how wonderful they felt. Next came a garter belt that she showed me how to fasten to my stockings. Next she handed me a pink thong that was just big enough to cover my stuff. "Always put your panties on after your garter belt. That allows you to be ready for anything that might come up." Next, she gave me a pair of pink, fluffy slippers "for lounging". Rhonda led me over to a table with a selection of various sized butt plugs. "It's important that we train your boi pussy to accept all "comers. You no longer have a penis, you have a clitty. You have a boi pussy instead of an asshole."

What's going on -- this is going to fast and too far, but I feel oddly relaxed and not able to relax. Rhonda selected a small butt plug, lubed it and brought it to my pussy.

She instructed me to relax and at first she worked one and then two lubed fingers into my boi pussy. Next she gently inserted the small butt plug. I felt odd, but very comfortable. It must have been too easy and too comfortable as she removed that one and inserted the next largest on. That one hurt a bit as it stretched me, but I soon adjusted.

Next was the pink lacy bra and then pink under bra corset that Rhonda cinched up tight.

Next she led me to the vanity where she trimmed my hair, I started to protest, but caught myself. This will help as it grows out.

"I will do your makeup at first, but I want you to watch closely." She proceeded to do, what seemed to me, to be magic as did up my face eyes and lips. When she completed my makeup she brought over a blond shoulder length wig. She applied a substance to my scalp and then carefully fitted the wig.

"There you go -- that wig will stay on for about a month so I will have to help you learn how to take care of it.

"Wait a minute", I said "a month?? I can't keep this on past tomorrow when I head back home."

"Relax, Toya you aren't going anywhere for a while. We have many surprises for you."

No! I said stop this now, give me my clothes back and let me go, I demanded. And what do you me 'We'?"

Rhonda grabbed me and led me over to what looked like a cushioned saw horse, bent me over and fastened my wrists on one side and my legs on the other.

"Let me go!"

"Let's quiet you down a bit", as she affixed a ball gag to my mouth.

You are going to be part of a niche network of 'Elder Escorts'

There are wealthy men who like to be seen with gurls their own age.

This allows them to be kinky while moving about their usual circles.

They pay our bosses quite well and they are also good tippers."

Rhonda stepped over to the wall and came back with a cane rod.

"First I am going to acquaint you with the consequences of willful behavior."

She reached between my legs and gently grasped my balls. Next, she squeezed them hard and I yelped into my gag.

Then, gently caressed my bum with her hands. Then there was a pause followed by a sharp sting. This was followed by another and another until I was blubbering into my gag.

"I am going easy on you as this is your first offense and you are of no use if you are all marked up. If you are ready to be a good gurl nod your head. I nodded and she released me from the saw horse, but kept the ball gag in.

"Time to dress you up sissy."

Rhonda brought out a pair of thigh high pink boots with 3" block heels.

"Put these on. The block heels will make it easier for you to get started."

Exactly what have I gotten myself into?

"