Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 3: Thursday Evening Negotiations
Erotica Sex Story: Chapter 3: Thursday Evening Negotiations - I thought my old college friend Roger would be my first and last time as a whore, but Cupid made other plans. The Joker took advantage by messing with my guy’s biggest client. I had to get this done or jobs would be lost. This time it was the real thing, I had to whore for a stranger who was known to pay more for a girl going outside the rules. A lot more. He was a nice older man who wanted my ass, and as an extra surprise he brought some family! (All over 18.)
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Heterosexual Fiction Sharing Slut Wife Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Sex Toys Prostitution
I arrived at the hotel, wearing the raincoat that covered my ‘spring picnic’ outfit. It was not raining on the sunless fall day but the raincoat made my attire acceptable for the location.
My plan was to use the house phone to call Mr. G to meet me at the elevator or tell me his room number. I felt uncomfortable walking into the hotel lobby with no undergarments on, I was sure people could tell somehow. Before me was a spiral staircase with transparent steps. A sign indicated the front desk was up the stairs. If I walked up those stairs I was sure people below me would be able to see my pussy and take pictures. That gave me pause.
Then I noticed some house phones near a bank of elevators on this floor and headed that way.
Apparently Mr. G was anxious to meet me, because when I approached the phone I recognized him converging. The “Kaiser’s General” photo my husband showed me was a good likeness, an older man, but still powerful and with a bounce in his step, so I smiled and moved toward him.
I greeted him by saying there was no need for him to come to the lobby and wait for me. He answered that he had just arrived, and confessed that he wanted to see if he could recognize me. “Mr. Maier had provided description, plus he mentioned a raincoat.” Mr. G showed my his phone, my husband had made a sketch of me in the raincoat and sent a picture of the sketch to Mr. G.
To make sure I was the right person he asked, “Did you know Mai ... or perhaps she used another name ... the girl who got married Monday?”
“Yes, we met several times. I am Evie, by the way ... I know I am a little older than usual...”
“Your age is not a concern to one as old as I ... and frankly you are more attractive than I expected. I know the last minutes change inconvenienced Mr. Maier, but fixing things is his job and he does it well. But I see you have two rings, are you married?” I was surprised that he noticed that detail so quickly.
I had decided not to wear my wedding rings, they were distinctive and noticed by the room service girl on the previous date. But I just felt wrong without something. After all, I was a married woman, so when I was naked in another man’s bed, giving him my body, I should have rings on. After Roger’s date I got a pair of simple rings, one with a natural black pearl as the engagement ring and a matching wedding band. I admit they were pricy, but after my first job as a whore I felt I had some free money. I had worked out a scenario about them. “I was married young, but it ended in an accident, so now the pearl ... The other ring was a gift from my husband well before our mariage. So they are not truly wedding rings ... If you would prefer I can remove...”
“No, please, do not on my account. I respect your feelings about marriage, now that you mention it I confess that I have considered the idea to honor my late wife. I do not know if I have been with a married woman since my divorce from my second wife, as most professionals do not advertise such details. It is not a concern, but sometimes I do wonder ... I am pleased you could share that with me.” His response put a bit of warmth into the meeting.
I used the opportunity to continue my story. “There is a man now, it might work someday but not yet. He travels. This opportunity came along, I am dipping my toe in this job. I admit that the appeal is not limited to the financial, I enjoy the variety when it works. He knows a little of what I do and understands ... for now.”
“You are fortunate, I do not mean to pry. My father’s generation would not understand, but your world today is so very different... ‘friends with benefits’ and unmarried couples co-owning houses ... But now I wonder, shall we proceed or...”
“Why thank you, I would love to see your room,” I said as I took his arm. I would say that we had made contact on friendly terms and based on his reaction taking his arm was the right move.
In the elevator he noticed the object in my ear, it was not a mass-market design. I said, “It is a temporary hearing aid, my ear was damaged at the gun range. We take all the measures, but sometimes accident happen. It will fix itself in a few weeks.”
“You shoot then?”
“Yes. I began hunting with my father when I was younger. First rabbits and fur bearers, then it was deers and wolves ... These days it is ducks with a shotgun.” That was actually true, it was a father-daughter date we kept each year.
When we got to the room it was time to show some of our cards and start negotiations. He helped me remove the “Paris Afternoon” raincoat, revealing my “Sunnybrook Farms” summer outfit. I posed. He appreciated the clever disguise needed to get into the hotel and gave a little applause as I turned around for him. He really liked it.
“Innocent and sexy, you have done a magnificent job bringing my dreams to life, you are quite acceptable to me. As to the concern you expressed, I hope I also prove acceptable. If you sit in the chair I can remove my pants and you may inspect as you wish.” The table had a basic NDA which I expected so I signed quickly.
I did not expect the quick show-and-tell, but reinforced how he did not like to waste time. It eliminated my question and he seemed willing. I sat. He dropped his pants. He was interested, his cock was almost fully engorged, tumescent but only about 20% stiff. He started to handle himself to show his fullest extent but I stopped him with a hand signal while opening more buttons of my top. After two more buttons my nipples were peeking out, after the third they were exposed. I usually wear B-cup bra’s, maybe a small C with some brands, but I knew my large puffy nipples were my strongest selling point. Usually I had custom bra to hold things up without hiding the central attractions, but with the backless top that would not work. My outfit changed that quickly from innocent to very seductive.
From little Mr. G’s reaction I would say he agreed with me, he virtually leapt to 50% stiffness. It was enough to see that his cock was a smaller than I was used to in both the length of the shaft and girth of the ridge. It was close to what I would call a torpedo shape so basic anal would not be a greater trial for me.
He stared at my nipples. “Such beauties my darling ... they will be a pure pleasure to worship. I am afraid that I will be inspired to a greater appetite than usual.”
“Well, all-night service means we don’t keep a count, our concern is providing quality for any quantity. I am content as to my concern. But I imagined some discussion first ... details as to specifics.”
“Yes, that is very wise, right now you and your lovely nipples have an obvious advantage over me.” He folded his pants and sat across from me at the table. That was when I touched the button on the phone activating the recorder. The battery would give me 8 to 10 hours of the “record and send” function, using my earpiece as a wireless microphone.
My husband had called during the afternoon with one important bit of news he had gleaned for just this moment. One of Mai’s friends recalled that three years ago Mai had agreed to a price of $2,500 for the night of “their usual activities.” At the time the overnight price for girls who played by the rules was set at $1,500, suggesting a 67% premium for the extra services she negotiated. Then next morning, as an extra tip for breaking the rules so enthusiastically with her anal cowgirl, Mr. G slipped Mai a half-ounce American Gold Eagle as a tip, added another $1,000 to that amount - a 40% tip at the time. (Gold is up significantly since then.)
I knew that since then the “normal” overnight pay for the contracted escorts had gone up roughly 60% to $2,400, that was ‘Evie’s’ gross compensation for that first night with Roger. (The escort business was legitimate enough to withhold taxes and sensible enough to match up to 10% of a tax-shelted contribution, so I did that. As I said, the girls held the power and they treated themselves well.) If Mr. G followed the pattern I could expect 167% of current base pay of $2,400 for a base negotiation target of $4,000.
I majored in Tax Accounting so I am pretty facile with numbers.
Mr. G had been nice so far, and I felt I needed to share something with him before we started to dicker. “Before we start I feel that I need to share one other bit of information about myself and my skills. I mentioned my late spouse, we did the usual things together during the marriage. However, my professional experience is very limited, as this is actually only my second session. So I really have to be clear that my skills, especially oral, do not measure up to the woman I am replacing.”
Mr. G put a positive spin on it. “In some things, when a woman is willing to learn, inexperience can provide an extra delight for the one giving instruction. I believe Mia did not discuss specifics with her associates, but I think that in terms of expectations, oral will not be a concern. To be honest, while it adds something at the start, I find other options have much more enjoyable outcomes. I confess, your unique charms may inspire extra efforts.” He gave a glance at my nipples, it was easy to imagining a tit-fucking. Maybe he was mentally broadcasting the idea. I kind of liked that.
He continued. “So let me start by saying that I accept your stated inexperience as a given without penalty, and your implied willingness. We are negotiating for the same activities Mia shared last year during our visit, in whatever quantity you inspire, for the entire night until 8 in the morning. Is that your understanding?”