I was fresh off my poker night stripper experience and faced with the prospect of providing escort services to Darren's friends. You'd think I would be overwhelmed and perhaps a bit trepidatious, but I wasn't. The only slight anxiety I had was over whether my full bore embrace of all these things suggested that maybe I was a psycho slut.
As I was thinking what sexual escapades the future would hold for me, I thought back to how I felt that day I sucked Darren's fat cock for the first time. At that time, I felt as though there had been almost a clean break from the old me to the new me. But now it felt a bit different. I was still a flirty seductress who wants to wield control over men with my sexuality. I had not become submissive outside of the very particular confines of my relationship with Darren. So, it was probably more accurate to say that I hadn't become a new person so much as I had shed the guilt and the cock tease aspect of my behaviour to embrace the slut that I have always been.
This occurred to me primarily because of the way I was thinking about my upcoming escort experiences. I fundamentally saw managing these men in much the same way as I had on poker night - sexually solicitous and generous but fundamentally in charge. Despite his condition that I be slutty and submissive, even Darren liked it when I was sexually assertive and reserved my submissive role for when it was just the two of us alone.
From that point on Darren and I grew much closer. Our Thursday evening dates more often than not involved some other activity -- dinner, a movie, a cruise on his boat, shooting some pool -- and were extended past the three-hour mark so there was still time for him to fuck me senseless. We openly discussed my escort activities, and it was a consistent source of stimulation for him.
Meanwhile my relationship with Pedro was sort of bifurcating.
We were fucking a lot more than we ever had, including almost every Thursday night after my date with Darren. I think there were a few things at play. My infidelity with Darren awakened some competitive sentiment in Pedro. The known fact that I was having sex with another man had the odd impact of mitigating Pedro's jealousy -- he no longer had to wonder, so that morphed into a sort of acceptance. And with that acceptance came a sort of resignation -- if he was to be married to a slut he might as well make sure he gets lots of pussy.
On the other hand, we were increasingly distant in all other aspects of our lives. Pedro had gotten a job in a retail store. This was facilitated by the fact that I had used some of my earnings to buy him a much-improved prosthetic leg and to get some treatments to help his back. He was still on light duty work, but at least he was more able bodied. That also is what facilitated an uptick in our sex life. In addition to spending time at work he was spending a lot more time with friends. His absence was notable at times, but I couldn't really begrudge him that.
I should also note that our sex life had improved in quality not just quantity. Between Pedro stepping up his efforts and eliminating some of his machismo tendencies/assumptions and my increasing comfort with my own body I was able to achieve orgasm with him sometimes. Beyond my own enjoyment, I have to say I was happy for him. Every man wants to know that he can bring his wife to orgasm and whatever else might be happening in his mind that was at least a win.
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After reflecting on it for a week, Darren and I talked about the escort thing again the next Thursday. I wanted to start with Reggie and Gerry. They were both single and I could easily have sex with them in their homes unlike Danny or Ricardo. I also found that there was something that didn't appeal to me about Ricardo. He was handsome and pleasant, but he was also a very stereotypical male. I felt as though it would be impossible for him to pay me for sex and respect me as a woman. I know that I am nobody's idea of a role model or a pillar of the community, but that doesn't mean I have to let a man put his cock in me if that comes with him viewing me with disdain.
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Gerry was above average in looks and obviously a successful guy. Nevertheless, he reminded me of all the men I had coaxed into happily serving my needs with my ample cleavage, short skirts and high heels. Like the landlords that I had convinced to cut me some slack on rent payments, the bosses who let it slide when I was late or made a mistake or the male customers that spent a little extra at the jewelry store just to have an excuse to gaze at my tits a little while longer Gerry seemed to just be happy to be near me and willing to let me lead him wherever I wanted.
I know that my experiences with those other men make me sound like a constant cock tease. But those situations weren't like it was with Darren back in the day. Those men had no reasonable expectation of having sex with me. They just enjoyed being around me and that is something that I have cultivated by making genuine efforts to be pleasant and sexy. I do it for myself too, but so what. A mature man doesn't look at a sexy friendly woman and think cock tease. He looks at her and thinks how much nicer it is to see her body, smell her scent, have her touch his arm or brush up against him ever so gently than to not have those experiences.
I picked out a black blazer dress from the extensive wardrobe Darren had bought for me. I wore my favourite black patent leather Louboutin's with the red sole and shear bra and panties in red. Dark eyeliner and red lipstick to match the shoes gave me a very dramatic look. Darren whistled and eyed me with lust when I emerged from the bedroom where he kept my wardrobe.
"It isn't your turn sweetie. But if your still up when I get back......."
"Oh, I will be here, Leti." Said Darren. Then he drove me to Gerry's house. It was evident to both of us, although unspoken, that me being an escort and him being my driver was a source of titillation.
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When I arrived at his door Gerry looked me up and down much the way Darren had. Like a hungry wolf looks at sheep. Then he seemed to catch himself and self-consciously apologized and invited me to enter. I smiled at his slight awkwardness not the least bit offended by the way he looked at me. After all, that was the reaction I was looking for.
With the door still open I walked in and put my arms around his neck and kissed him full on the mouth. I wanted to start off on the right foot and I liked the idea of Darren seeing that before the door closed behind me.
Gerry looked towards a stack of cash on a table in his entryway - $500/hour and a three-hour minimum were the terms. But before he could say anything I took his hand and lead him into the house saying, "We will deal with that later."
"Can I offer you a drink Leticia?" He asked nervously.
"Yes, a white wine would be nice." I answered as we both walked towards the kitchen. 'You seem nervous Gerry."
"I am. You however don't seem nervous at all."
I laughed. "Were you nervous when I gave you a lap dance at the poker night?"
"Not so much. I just all happened so fast. But this I have been thinking about for a while. I want you to enjoy yourself. And I have never had an, uh...."
"Escort? You've never hired and escort?"
"That is right."
"So, why does that make you nervous? I mean I am a sure thing."
"Yes. I suppose that is true. But I meant it when I said I want you to enjoy yourself because I like you. But I also know that you are here because I am paying you, so um...."
"How do you know if I am having a good time or if I like you when I am paid to be here. Is that what you are thinking?"
"Yes. Kind of."
"I do like you. I wouldn't be here otherwise. Gerry, believe it or not I am sort of new to this. Reality is that I do it because I enjoy it, and I love sex. But I only enjoy it with men that I like. I wouldn't be here if I didn't like you. $500 an hour isn't the price of an escort that must take on any client who asks."
"That is true." Said Gerry as he handed me my wine. Again, his eyes drifted down to where the edge of my bra peaked out from behind the open neck of my blazer dress. He blushed slightly as he saw me catch him looking at my tits.
"It is ok. I picked this outfit for you."
"How so?"
"Well, I try to pay attention to the way a man looks at me. I've always enjoyed attracting the male gaze. Not that I know what you would like. But based upon our last meeting I thought that this outfit would best highlight the parts of me that you find appealing."
"You nailed it. But then I think that all of you is appealing. I can't really imagine anything you could wear that wouldn't be sexy as hell."
"Thank you, Gerry. I have never really understood women who are offended by the male gaze or expressions of desire. I mean don't be creepy of course, but I like that men want me. And I have always enjoyed dressing to complement or even show off my body. So, feel free to look at me and talk to me about what you really want."
"I've never met a woman who is direct about it like that."
"Well, I am not like this always with everyone. But we both know why we are here, so I think it is easier and better to be direct. So, you said that you have been thinking about this date. What do you want to do with me?"
"What don't I want to do with you?" Came out with obvious enthusiasm for any sexual activity I would allow.
"I appreciate that. How about what is something that really appeals to you or which you have really thought about?"
"I really want to eat your pussy."
"Hmmm, one of my favourite things. Do you want me to lie back and spread my legs for you or bend over so you can eat me from behind or sit on your face?" I asked before leaning in to kiss him again as we stood in front of each other in his kitchen.
"Oh fuck, I can't believe the way you just say it like that. Damn you are sexy."
"Take your pick Gerry and we will start with you eating my pussy."
"I want you to sit on my face."
"Alright then. Take of your clothes."
"Now?"
"Yes now. You have seen me naked. Now I want to see what you have to offer." I responded with an intentionally commanding tone, thinking he would like that.
Based upon how quickly he stripped off his clothes, I was correct. I just sipped my wine and watched with contented amusement as he obeyed my direction.
