She gently touched my shoulder when she said "Hello".
I was already seated. She was standing next to me, getting ready to seat herself next to me at the corporate table. The front of her dress was right in my face. She slipped between the chairs with her thigh slightly bumping my face as she moved in. Her dress swished across my face as she sat down. She was so close I could smell the sweet fragrance of her perfume. She smelled nice.
I knew she was trans. Everyone did. She kept to herself in the corporate office. She had helped start the company. She was a founding partner, and the CFO. I was thrilled to be invited to the head table. Only 8 of us were seated there. I'd been promoted and the dinner tonight was a celebration of a great year, and to award a few of us for our efforts.
I'd never been this close to her. She is pretty, polite and professional. Probably in her late 40's. She is a fairly large person for a woman. Six foot 3 if she is an inch. Tonight, she is in a purple evening dress. It fits her curvy body nicely. As she moves the hem of the tops of her black lace stockings and the tops of her black lace bra slip in and out of view. Her legs are long and shapely. She is sporting back seamed black nylons tonight. Very retro, and very sexy. She has pretty large breasts. Or at least that's the look she is going for. Who knows if she has had them added, or if she just has some silicone breast forms tucked into her black lace bra. Her face and hair are smooth and fresh. For a guy, she has always been pretty. Her red hair softly flowing over her bare shoulders.
It's hard sometimes to tell yourself she isn't really a woman. She is rich, powerful and holds my future in her hands in a way. Maybe I'll have a chance to thank her. maybe she shows some interest in me. Maybe I'll be a big wig in the company if I please her. I find myself gazing at her, wondering. I look up and down at her, wondering what she is really thinking of me. I dream of being her vice president. Or maybe her lover. Or both. It's interesting how power and money change your perspective of someone.
But, of course, the chances she is packing a big 'ol cock in those panties, somehow ruins the fantasy. None the less, she looks pretty good.
She doesn't talk with me at all during the dinner and awards. When things are breaking up, though, as we are standing alone outside the door, she takes my arm, gently leans in, asking me three simple questions.
"You are alone tonight, right? You're single?"
I sheepishly nod, yes.
"You've done a fine job this year. I'm proud of you. Did you enjoy the evening?'
I look in her eyes as I quietly say, "Yes, I did."
"I'm glad. I have one more award for you then. Would you like to have it?" As she asks me the question, her grip on my arm tightens. I feel her other hand slide across my back, holding me closer to her.
I look at her again, with a questioning look on my face. "What sort of award?"
Her hand moves around in front of me, then slides down over the front of my slacks. She presses against my crotch. Her grip on my arm tightens. She slowly pulls my arm back around behind me, gently nudging me back against the building wall. I'm pinned against the wall, in her grasp. But I didn't resist.
"I couldn't help but notice you looking me over tonight. I wasn't sure if I was comfortable with it. So, I thought I'd ask."
Her hand presses in a bit more into my crotch.
"This sort of award. Are you interested?"
We are face to face, nearly the same height. Her perfume is sweet. Her lipstick glistens in the dim evening light. I have a pretty good look down her dress into her cleavage showing off her sexy satin and lace black bra. But I know this isn't a regular sort of thing that might happen. I'm confused. But, to my surprise, my cock is getting hard. I slowly nod my head. I can hear myself quietly whisper to her. "I think that would be nice."
What is going on?
As she is leading me back into the parking garage, she lets me in on a few things she says I need to know.
"Remember, Bill, I'm your boss. I'm in charge, I'm in charge of everything."
"Of course, Ma'am."
She liked me calling her Ma'am.
Just before she opens her car door, she pushes me around, pulling my arms together behind my back, and cuffing them.
Who the fuck had handcuffs in their purse at a company party?
Well, she does.
"Another thing you need to know. You're my bitch. I'm going to make a real man out of you, but you're still my bitch. get it?"
No, I didn't get it. But once we were in her car, she went down on me. Sucking the juice right out of me like a pro. Her dress was undone in front to the waist, her bra undone, exposing her more than ample breasts and huge, erect pink nipples. She wrapped them around my hard cock, tit fucking herself before finishing me off with her vacuum sucking mouth and relentless tongue. I didn't seem to care that these might be fake breasts. They were big, soft and felt like real ones, the bast I could tell. I blew a huge load that she swallowed without hesitation.
As she was buttoning up the front of her dress, adjusting her bra back in place and licking her pretty red lips, she asked if I liked what she had done.
I was on my back in the front seat of the car. My arms were still cuffed behind me, but I didn't care. My pants were pulled down around my ankles. My still half-hard cock, shiny with wetness, was waving in the moonlight. I had a very surprised and thankful smile on my face.
"I guess you did. There is a lot more of that ahead for you, Billy. Are you up for that?"
I was in shock, I suppose. I just nodded. Then just like that, we were off in her car, heading to my next adventure.
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