Meeting Charlotte Pt. 01

"Finish your wine, please, and then focus everything on the ring. It is so pleasant, so warm. You want to relax and just listen to my voice. Will you do that for me please, Charles? We're just two people, getting acquainted. I just want you to relax. It's so pleasant to relax. So pleasant just to relax and listen. And the more you do, you find yourself feeling more and more warm and comfortable. Breathing slower and slower. So pleasant, so warm, so relaxed," he said smoothly.

"Mmmm-Hmmmm," I breathed.

"You find that you really enjoy this sensation very much. So very, very mush. This pleasant floating, listening to my voice, being guided and directed by me. In fact, you'd like to experience this again, wouldn't you? You've never felt this relaxed. And since I've shown you how to feel this way, you will have no problem letting me do this again will you. You'd like that? To feel this way again? To feel even more relaxed and directed? The proper response now is Yes Sir. You were military; obedience should come naturally to you." His voice was again instructive.

"Yes Sir," I agreed.

"In a moment I am going to leave. There will be a card in front of you with an address. Be there at nine sharp. Again, the proper response is Yes Sir."

Again, I responded. "Yes Sir."

The last I heard was, "Count to 60, then take the card. The bill is paid."

__________

At 8:59 I rang the doorbell. After leaving the Hilton I had gone home, calculated the travel time and then sat and read until time to go. I gave no thought to what had happened; it was a fog. There was only my obligation to be at that address at that time. It was no different than an order or a class assignment.

He opened the door and smiled as he stepped back for me to enter.

"Right on time. That's very, very good. I'm pleased," he said as he put his hand on my neck, lightly steering me into a living room-den-library set up. Large couch, overstuffed chairs, a desk, a fireplace with large screen, and stuff on shelves. He led me to the center of the couch and with his other hand clicked a remote. The screen lit up with a swirling Mobius strip in smoky dark blues and greys.

"Like the reflection in my ring, you will find that as you watch the screen for just a few seconds, you are captivated. You cannot look away. All that exists is the soft, slow, sensuous motion. It is so pleasant to watch. So pleasant to listen to my voice." His voice was so soft but firm.

"And so the longer you watch, the more relaxed you become. So pleasant to relax, to just watch, to just watch and listen to me. No separate thoughts, just my voice. Don't you agree it is so pleasant to just sit and watch and listen and answer?"

I knew the response should be, "Yes Sir."

He talked further about being open and trusting, relaxed and open, aware but no thoughts other than what he said and asked.

My only thought was to agree, "Yes Sir."

He was quiet for a while as I followed the endless swirl of the strip. The colors were like smoke mixed with dark eyeshadow. I was aware of someone in one of the chairs, but it was dark. And the screen held my attention.

As I waited for the swirling emptiness to be filled, I could hear soft voices

Female -- What have we here?

Male -- Male, late 20's, fit, trim, well dressed, new in town, no ring, very susceptible.

Female -- Nice. He's cute enough but not twinky. How far did you get?

Male -- The ring took him right under, and he is totally absorbed.

Female -- Let's see what we've got. We're running out of time.

"Charles, this is Vincent. We met at the Mall, shared some wine, and I invited you over. Do you recall that?" The male voice was firm.

"Yes Sir."

"And we decided to continue the conversation at my home where we could talk in private, just like the friends we are, right?"

"Yes Sir."

Female -- Respectful. Southern? Military?

"So Charles, you grew up where?"

"South Carolina"

"Your family is there?"

"Just my Mother and me."

"And after high school what did you do before Denver?"

"Air Force. Supply for four years. Loadmaster for four more. Then grad school."

Female -- Hah. Southern, Mother's Boy, Military. Knew it.

"What brings you to Denver?"

I got hired by Martin-LOGEX and moved here for training.

Female -- Oh! Oh, uhh OK. Means he's here till mid-January. Keep going.

"So Charles, are you married, engaged, girlfriend?"

"No."

"When did you last have sex with a girl?"

I paused. "I haven't."

Female - - He's Gay?

"Why not?

Again a pause. "I have a very small penis."

Female -- What?

Male -- Will you chill; let it play out.

"How small? We're just friends here. Relax for me. Friends can tell friends things.

A sigh. "Very. Less than an inch."

"So you have been affectionate with women, but no sex?"

"Not really; no use; they'll find out."

Female--- He's Gay. This works.

"Are you Gay?"

A longer pause. "I don't think so."

"You're sexually attracted to men?"

Again a long pause. "No."

"Have you had sex with a man?"

A longer pause

Female -- He's Gay through and through. He's just repressing it. Pull it out.

Male -- Easy. He's way under. There's no deception. He's just holding it deep.

"It's OK. Was it a teacher or coach or neighbor? It's no big deal. We're just chatting."

A longer pause. A sigh. "My Great Uncle"

"Ah. Thanks. How young were you?

"A month ago."

Female --What? Last month? And he's not Gay?

"That's interesting Charles. I know you have been holding it in. Share with me please. Friends share. You'll feel so much better if you do not hold it in."

His voice was firm. "You cannot resist. You are so deeply under my control that you must answer. Tell me.

And so it just rolled out. "Somehow Georgia Tech accepted me for a Masters. My Mother's Uncle lived in Atlanta, and he was willing to trade room and board for chores. She is his only heir, and she is counting on inheriting to give her the financial security she's never had. He has always been single, and I never thought much about whether he was Gay or not. None of my business. After I was there for about six months he became more touchy, as did his two friends who visited often. Then one night he made a full pass at me and when I resisted, he reminded me of my Mother's financial status and suggested I consent. And so he taught me how get him and his friends off -- either with my hand or my mouth or my ass. There was some bondage, and one of friends liked for me to smoke while sucking him off. When I graduated, he told me Mother's future was secure. The last week, he fucked me in the ass every night. But then the day I left, he gave me $10,000 and told me I was welcome back any time. There were also checks from the other two for $5,000 each."

Female -- Holy shit!! So he knows how to give and take. And he's still this soft looking?

Male -- I think we can feminize him easy. He's practical. He's reward driven.

"That's interesting Charles? So you submitted yourself to your Uncle and his friends for the benefit of your Mother?"

"Yes."

'Did you think of yourself as a whore?"

"Yes. Pretty much"

Did they call you names and degrade you?"

"Yes. It was part of the deal."

Did they make you dress up in women's clothes?"

"Panties, hose."

"Make-up?'

"No, but they liked my legs shaved, which I did for cycling anyway."

"You smoked because they made you?"

A bit of a pause. "I felt sexy; like a prostitute; it really gave me power over the one guy. I convinced him to buy me some clothes."

Female -- Now that's interesting. Not totally submissive. Turned it to his advantage.

Female -- Any other leverage?

"Charles, do you do drugs?

"No."

"Gamble?"

"No."

"In debt?"

"Grad school loan."

"Charles, settle back and watch the screen now. Think of nothing except how pleasant my voice is. It's pleasant to do as I suggest. No worries; no concerns; just my voice leading and guiding you.

Female -- He's what we need to replace Jason---God how close we came to getting nailed for his dealing. Let's take him downstairs and see if he is malleable. I mean it sounds like he was a quasi-whore to protect his Mother. And whatever it is with his dick, he's probably got lots of repressed sexuality.

Male -- Don't push it.

Female -- Look. If he fits in with Mia like I think he will, the views will surge. He's a puzzle -- All-American boy who's never had a girlfriend much less been laid and then blows his Uncle and friends to protect his Mother. But knows what and why he is doing it. He's only here for six months though.

Male -- We both know this gig will run as long as we provide what our particular demo wants. Competition is beyond brutal so we need to make what we can before we lose our share..

Female -- As your CPA, no disagreements here.

Male -- OK. Let's go downstairs.

Victor told me to rise and follow him. We went to the hall and then down the stairs to the basement. At the bottom, he turned on the lights. Zoned out as I was, I saw it was cut into sections with little stage settings. One section had clothing racks and dressers. Another had a mirrors and lights and chairs. There was a bedroom set, others with benches and chairs. It was a lot to take in.

We stopped in the middle, and he pulled me close.

"Look at me; look hard at me and listen and obey. You are an attractive person. I can see why your Uncle and his friends had you service them. So we want to give you a chance to realize your potential. To give others the thrill you gave them. There's a subtle sexiness about you, and we want to enhance it. So you will obey us and learn. Is that understood?"

"Yes Sir."

"So, you become more alert now, more awake, but still totally under our control. You will obey us; you will not refuse us; you will do as instructed without hesitation. Is that understood?

"Yes Sir."

"Fine. This lady is my associate. She will instruct you now."

I looked over. This must have been the other voice I was hearing. Although lost in concentration on the screens as I was aware of what they were saying, and I had a sense of what they wanted. A little thrill went through me.

She stepped in front. A bit shorter than me, fit, trim, short auburn hair, greenish-brown eyes, thin dark lips, a hint of cleavage in a crop top, stretch jeans, black pumps, attractive but not hard, serious but not bitchy. Think Phoenix in Maverick - Top Gun.

"Get undressed all the way. Put your clothes and shoes there, then stand in front of me," she ordered.

I returned. Feeling the goosebumps starting to rise, I put my hands in front of me.

She now had a little crop and she smacked my hands, "Put your arms by your side," she snapped.

I complied, waiting as she circled me twice, tracing my body and limbs. She then stopped in front and slowly brushed my penis with the strap.

"What's this?" she demanded.

"It's all I have," I said.

It was brief, but she flinched---like she wanted to chuckle, but instead allowed herself a little smile. It was endearing, but moreover it told me that like my SERE training, this was staged. Endure, tolerate, do not give a reason to be punished, stay in character, don't lose yourself. All underneath a strong compulsion to obey. It was easier to obey.

"It looks something like a penis but it's so much smaller," she observed.

"But it still works," I replied, earning a smack on my thigh from the crop.

"That wasn't a question. You speak only if I have a question," she emphasized.

And so the game begins.

"So what did you say caused this?" she asked.

"It's called a microphallus, ma'am. I was born that way. Genetic hormone imbalance I 've been told," I replied. "Same thing that gave me 2% body fat and being able to run a 33 minute 10K. Not that either of those are a marketable skills."

"Sort of like the Johnny Cash song about a boy named Sue," she replied.

"Well, my Father was never around, but I don't think he intended to leave me with that. It wasn't until high school with the communal showers that it got a little tough. But I ran varsity track as a freshman and my cousin was the left tackle and shot-putter so nothing got too far out of hand. And only a couple of girls wanted to go out just to see it."

"So you're still a virgin."

"In that regard, yes ma'am. But not oral or anal."

"Do you beat off? Well, not so much beat as stroke," she sort of giggled.

Another small opening. "Rarely, the endorphin release from a half or full marathon has a lot in common with an orgasm."

"Well, let's see." She took the crop and pushed me in the chest hard enough to make me step back.

"Up there," she gestured. "In the chair. Sit and don't move."

She Velcroed my legs in place, went to a small night stand and came back with a bottle.

"Right or left handed?" she demanded.

"Left," I mumbled. I dropped my head, repeating the SERE mantra as the humiliation rose.

She poured some in my hand. "Too much?" with another twinge of a grin.

"Mmm," I said.

"Good point," she said as she went back to the stand and pulled out a ball gag. She grabbed a cloth out of another drawer.

She dropped the cloth in my right hand and as she fastened the gag, she said, "Catch your cum in the cloth and then eat it."

She then got right up against my ear and whispered, "You may not recall, but while Victor had you in the trance you admitted to eating other men's cum and that you saw yourself as a whore. So be a good little whore for me now." She then smacked each of my thighs with the crop.

My head jerked and that's when I noticed Victor had set up a camera. I shook my head in protest and got two more slaps.

"You're going anywhere. You're going to stroke that little thing until you get off and then eat it!" she hissed and then hit me twice more.

So help me, the first thing I thought was I'll have to wear bike shorts on the run to hide welts. She raised it again, and I nodded vigorously. And then I got to it.

Masturbating my cock was simple -- thumb and forefinger. Like rubbing a worry stone. She was watching over my shoulder, giving little moans in my ear, running her nails on my neck.

It was very effective. Two minutes, maybe three, the tingle started, and I stiffened.

"Catch it all," her breath was hot in my ear, and she let the gag loose.

"Eat it!"

My ears were roaring. I had never cum like that---ever.

The crop smacked my back, and I licked away. Five quick ones, then a sixth to make sure I had it all.

She murmured, "Nice." Leaving me restrained, she went down to talk to Victor.

Moments later she was back.

"So here's the deal. On the surface we model Crossdresser stuff for catalogues and websites. But we just also so happen to have a need for someone who is Gay and a Crossdresser. You fit both. A little makeup, prosthetics, wigs, and you'll do nicely. The other part is we broadcast a BDSM Pay-Per-View on Saturday evening. You're single, not dating and no doubt all that running has given you a tolerance for discomfort. You admit you've served as a male whore for compensation; this is no different, other than you actually get paid. The more views, the better we all do. I'm the accountant and I make sure it's equitable. Beside that small dick of yours may get us even more hits. You have 10 seconds."

I used the full 10 seconds, mostly to look at her. She was very pretty. "OK," I said. I guess this is certainly confidential, but not illegal?"

"We're all over 21; no drugs; no trafficking; I issue 1099s. But we are discrete. And Victor will talk to you upstairs as necessary if your conscience needs shoring up. He's pretty persuasive. He could have you walking down Colfax naked in 10 minutes. But the bottom line is, it's just business."

I nodded. "What next?"

"Be here Wednesday at nine," she checked her watch.

__________

And that's how it began

So here we are three months later. Work is hard, purposely hard--like basic. I've been humping 12 hours a day during the week and then six hours on Saturday learning the Company from the basement up. Sleeping, eating and training used up most of the rest of the time. Sunday was a free day but I found myself logging on mid-afternoon. Going out took money; dating took time and as previously noted, I would be investing in a dry hole after appropriate choking laughter. So Saturday was just another night.

The modeling was not too hard. Relax, look natural, and don't look at the camera. Crossdressing was no big deal. Heels were difficult at first, but being slight, things fit pretty well. And I shaved my legs for cycling anyway. Having a runner's chest meant the breasts fit well.

Victor worked in fashion which is how he got the modeling work, friends of friends I suppose as this stuff is only available online. He also has make-up skills and worked for several department stores. We planned the show on Wednesday after modeling, and then Saturday prep took about an hour usually.

But the actual shoot, that was harder than it looked. Sure Uncle Ralph and friends had used me both ways, but they were guys in their 70s and even as slight as I was I could push back if they went too far. But 90% of this BDSM was pretty real -- sometimes uncomfortably real----last two miles of a marathon real. Mia and I worked on her pulling the slaps, but some of the restraints and positions, well let's say my expressions of pain were real. Most of the times it worked. When it didn't, I had Sunday to recover. Or blame it on being out in the sun.

By mid-July viewership was up. And my pay increased. There were also bonus sessions such as when in response to requests, Mia brought a friend, and I got it from both ends. My paycheck for my efforts on those shows was doubled -- again no pun intended. By August, Georgia Tech was paid off, my IRA was maxed so I'm researching municipal bonds, quarterly income tax paid, money to Mom every two weeks, and I wasn't touching Martin-LOGEX's money.

Oh, and the essential point of this entire retrospective -- Charlotte's unknown issue -- so I had to play along. The Wednesday after Victor's reinforcement session, I politely asked if I could speak to her for a moment. I apologized if she thought any of my behavior was inappropriate or not respectful. I told her I appreciated this opportunity to supplement my income and get out of debt before starting a new career. She nodded and turned away.

And so other than holding the door for her if we happened to be there at the same time, I stayed low-key, did my job, cleaned up afterwards, was polite, and left quietly.

Still, I found myself staring at her when she was not aware and wondering what gives. What if, what's going on, what's bothering her, etc. And it was prominent in my thoughts on my commutes, runs and rides, and the quiet time before sleep.

I had a crush. A growing one. A serious one. A real serious one.

And no chance or hope of acting on it.

Until ...................the first of November.

Continued in

MEETING CHARLOTTE PART II - I BOUGHT HER MOTHER CHAMPAGNE