How I Became Carl's Whore

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And so it came time for the first 'date'. Instructions were texted as to time and length of the visit, what to wear and the role to adopt -- shy or direct, casual or formal or athletic, drink or smoke, clean or make-up. The meetings were at one of two hotels in the bar or patio as weather dictated. The 'date' would have the key. Make small talk, maybe have a drink, go to the room only when the 'date' said he was ready. I was nervous of course, but once in the room and finally getting his cock in my mouth, it all worked -- my flirting and encouragement; his ejaculation.

Carl would come to my house once a week, and after a cigarette, a drink or two, and reinforcing triggers, he would give me feedback on the 'dates'. The first time I recall thinking all managers are the same, regardless of the business. Later on, it was just routine.

I'm not sure when I understood why I had let myself turn into a whore. I was alone, but not lonely. Carl's cock stroking and seduction were mesmerizing, but somewhere I knew that a person could not be made to act against their interest. I wasn't bored; I had plenty of things to do. It wasn't money. Carl never offered and I never asked. It was the thrill of being naughty: smoking, make-up, hose, making men cum under my control.

The clients for the most part were pleasant--nervous usually, but pleasant. A couple needed some encouragement to tone it down. Ranger school taught me that posture and attitude can be just as persuasive as an M4 in your hand. And then there is this lady who comes to town every couple of months. She puts her make-up on me and then a wig styled like her hair followed by a ball-gag and cuffs. She fucks my ass until I cum and then makes me kneel in front of her as she masturbates. We then have lunch and chat like old friends.

But then a couple of months ago, I had my annual check-up. I had always thought the doctor lingered a little bit on the prostate exam. So this time I clamped down as he withdrew and pushed back as he exited. On a dare, I turned around as said," You should use two fingers, I think that might let you be more thorough." He just stared. Lowering my voice I continued, "Or you could use something a little bigger and more sensitive." Blushing, he stammered, "that's, that's not appropriate." "Just teasing," I said with a little pout. Later that day, his office called and said the Dr needed to repeat one of the exams and could I be there at eight. At 8:10 the next morning he was cumming in my ass. I gave him Carl's number and we've 'dated' a couple of times.

I could go on but after a while they fall into certain patterns and I have worked hard to recognize and adjust. My goal? To understand why I am a comfortable with my life choice. Thanks for listening.

POSTSCRIPT: I sent the foregoing to the therapist. We discussed it generally a week or so later at the next session. He was supportive but a lot was unresolved. So a week after the session I'm outside at the bar patio, nursing a red wine (as directed) and wearing bicycle shorts and Polo shirt (also as instructed). Someone approaches from behind and pulls out a chair. Guess what? It's the therapist.

"Hey Dr," I say as I stand up. "Taking a late lunch?"

"Not really," he says looking around and then shrugs. "More like an afternoon snack."

"Uhhh, I'd ask you to sit, but I'm scheduled to meet someone; you know-----."

"Yeah, I'm your 'date' as you delicately phrased it."

Insert moment of silence while I process this at the speed of heat. "Doing a field test to assess my issues?" I shoot back. "Or an existential analysis of this reality?"

"More like looking to better understand the stimulus/response reactions"

"That's pretty easy actually; the 'dates' have a desire or a need or a fantasy and I respond as best I can."

"Actually, it's the stimulus that makes you respond." And with that he put a pack of VS 120s on the table, pulled one out and began stroking it. After a few strokes, I found myself sitting back and watching.

"That's right," he semi-whispered. "It is so very hard to look away. Just like Carl's cock when he strokes it, you find yourself captured and enthralled. That's such a descriptive word isn't it---enthralled. Would you repeat it with me?

"Enthralled," I sighed.

"Yes, and because you are enthralled and content, I need to get you to agree that despite our professional relationship, it's OK for you to keep this 'date' with me. Your relationship with me can be both therapeutic and professional. Agreed?"

He kept stroking. I agreed.

"And that's because you have become a professional escort and as we have discussed you are comfortable and accepting of the changes Carl has made in you. Agreed?"

He kept stroking and again I agreed.

"Now, what did Carl tell you about this 'date'?"

"Biking shorts, tight jersey, light make-up, oral, cum on my face," I replied.

"Excellent," he said. "Perhaps you'd like to apply some lip gloss and I'll light this for you. You told me how sexy it is when you leave a lip imprint on the filter. And then later on my cock, isn't that right?"

"Whatever you want, sweetie," I said getting into character.

"And you have no problem whatsoever with performing?" he asked, still stroking the 120.

"None; I'm at your disposal for the hour or until I make you cum," I replied, slowly applying the gloss and then reaching for the cigarette.

It took much less than an hour. I had barely freshened my lip gloss before he started leaking. 10 deep strokes later, and he was bouncing on the bed. Two more strokes and he let go four shots which I maneuvered to both cheeks. He was still gasping for air as I wiped my face and cleaned my fingers. I left him still laying on the bed, telling him to see me downstairs.

I was on my second glass by the time he got there. Lighting up, I exhaled a couple of times in his face and then relented. We agreed I could see him or he could book me, but not both. A week later, Carl sent me a text for a repeat performance.

*********

I went to see a counselor to figure out why I have no--or very little--guilt over my conversion. Katie is in Korea for another year, and I'll try to explain to Charlotte when we meet again. Getting fucked, orally and anally, by strangers and regulars alike is indeed risky. I'm not paid for the 'dates'. Don't need the money and somehow Carl's control suppressed that issue. So what if a consenting adult subscribes to a dating service with benefits. And to be sure smoking is bad but it's only a couple every few days, and I can still rides 60 miles in under 3 hours. Life on the whole is good.

On the other hand, that's just a bunch of lazy, convenient rationalization. Truth is, I enjoy being a submissive whore. Call Carl and come see me.

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AnonymousAnonymousabout 1 year ago

I then picked up the lighter and VS120s and walked slowly back to the kitchen, taking deep breaths. As I came in he looked me over and nodded appreciatively. And when I pulled a cigarette from the pack and gave him the lighter, he said gently, "so you've gone all the way?"

"Yeah," I said, exhaling towards the ceiling. "All the way."

* * an ex girlfriend feminized me and once she got me hooked on VS120's, all my feminine mannerisms just came naturally. i held my cigarette in my fingertips, limp wristed, taking long deep drags and making eye contact as i exhaled. I found out later that my smoking was an asset as i would only suck cock if i had my VS120 in one hand while i stroked with the other. Its empowering knowing that i can attract me being a crossdressing slut now. She was my last girlfriend. I only date men now. Yes, I am gay. So glad she seen in me my potential to be a sissy cocksucker. I am one lucky gurl.

XOXO - GAYle :)

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