Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 2: Getting to Something Different
Erotica Sex Story: Chapter 2: Getting to Something Different - 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
(This chapter is background and has no sex. Clothes come off in the next chapter.)
Over the few weeks after my night with Roger, my husband had several big customer visits that went very smoothly. He had no trouble getting his clients quality professional escorts from the service. But smooth sailing meant the trail of whoever targeted my husband had run cold. There was some investigation from the Chamber and their off-duty cops. We knew the problem was deliberate, and that somebody within the escort business supply chain was involved. It seemed like more than any one person could pull off. The big break was learning that some of the girls had been paid “flash money” to say they were unavailable as escorts for the date of Roger’s visit. The girls were promised future payments, but those were not forthcoming, leaving all the girls with a bad taste in their mouth. But since they were betraying their union they were not eager to talk. After that there were no new leads.
Everybody involved in the case was calling the perpetrator “Joker.” If there was an associate (which seemed likely) the name “Gaga” was used.
On another front, things were looking up for my husband’s career. He was bring in more business than expected so he was at the head of the line for a promotion in January. Roger’s enhanced order plus the bonus interception padded Tracy’s lead.
My husband’s biggest client was a Mr. Gagne or as he liked to be called, Mr. G. He came to town once a year, but was the biggest customer of the firm’s most profitable product. Mr. G’s business was critical, the bean counters said he accounted for 20% of the EPS. I was told that was important. (One of my profs in college talked about the importance of EPS, he could go on forever, but I just could not get into it.) Tracy’s bosses thought this client was important enough that my husband called the firm’s VP-Operations directly with the shipment schedule as soon as Mr. G left the office, so he could schedule production over the next 15 months.
Tracy took over Mr. G’s account five years ago. An usual series of random events (a surprise retirement, random illness and vacations for senior sales staff) put Tracy, a junior associate at the time, taking the meeting with the firm’s most important client a few years earlier than expected. But my guy was up to the task. Normally sales people do not deal with the production bosses, but Tracy did the extra work and Mr. G appreciated the effort.
The negotiations went so well that Mr. G insisted on dealing with Tracy exclusively, he told the bosses that it was Tracy or he would go elsewhere. That was when the company promoted Tracy to a senior associate over several others.
Tracy’s first contact with Mr. G was at a bar, where he introduced the client to a new escort named Mai Vee. There was minimal social time, Mr. G was eager to enjoy the escort alone in his room. Mai Vee also seemed eager. Tracy felt his presence was no longer required so he left the two to make their private arrangements.
Mai Vee and Mr. G both knew about the usual arrangements regarding money and union rules. But Mr. G suggested that he had some desires the Union didn’t like, and he was willing to pay for what he wanted. Mai was more flexible about such things. They quickly reached an agreement that “maybe those rules are for other people.” Also, “I won’t tell if you don’t tell.”
The next morning in Tracy’s office Mr. G reported that he was more than satisfied with Ms. Vee. In fact, he insisted that for future visits he would make his own overnight arrangements directly with her. Tracy arranged for the company to pay Ms. Vee the standard payment, taking care of the union fees, but Mr. G’s private arrangements were “off the books.” Tracy presumed these ignored the usual union rules, but he covered the arrangement, keeping everybody happy. After that there was private contact between the Mr. G and Mai, Tracy only saw Mr. G at his office for their negotiations. Mr. G even took care of booking the room at a different hotel. Mai checked in with Tracy before and after each meeting to deal with the routine paperwork, but private acts and extra compensation were “don’t ask, don’t tell.”
Mai was very disceet. All anyone else knew for sure was that all sides were very happy in the morning. From gossip about normal ‘girl talk’ over the years Tracy reinforced his impression that Ms. Vee willingly did things outside the rules, but it was nothing harmful and she was well paid.
Tracy and his employer considered Mr. G an unlikely target for the Joker, because Mr. G made his financial arrangements directly with Mai.
But the weekend before Mr. G’s Thursday arrival, a pesky Cupid intervened. It seemed that Mai Vee met an old client on Friday, stayed with him all weekend, and was persuaded to marry him on Monday. Mr. G was the first person Mia called to say their date for the upcoming Thursday was called on account of a lovely marriage ring.
Mr. G was happy for her, he sent her a wedding present and sent Tracy a note asking that he make another introduction for Thursday. Tracy got right on that request.
Somehow, in the brief period between Tracy getting Mr. G’s request, and the union’s nominating replacements, the “Joker” intervened and killed Tracy’s request. So Tracy was unable to make arrangements with any of the girls he would entrust to handle Mr. G overnight. Tuesday evening the escort company informed Tracy that all the girls he listed were booked or unavailable.
Tracy started to make his own calls. But it was short notice (less than 48 hours), plus the coming Thursday was already heavily booked with regular clients, so the best girls were already committed to legitimate dates. Those few who were not already booked expressed concerns about what Mr. G might want, since his name did not come up in the usual girl talk except that nobody knew the specifics. Perhaps Ms. Vee and/or the Joker had allowed some unsavory rumors to spread. Tracy was not sure if this was legitimate problem or another attack, but by Noon Wednesday the fact was that nobody Tracy trusted was available.
Finally Tracy’s boss came to him, explained that the “people upstairs were concerned” and said he had to pull another trick from his hat, “like he had with Roger.” The corporate thinking upstairs was that if one miracle was possible, two miracles were routine. The boss expressed confidence, but again he had to be kept out of the loop.
My husband called his “last resort” girls, mostly retired escorts, but had no takers. However, one former roomie of Mai suggested that Mr. G’s requirements might include anal sex, which was against the escort union rules. The suggestion was that Mr. G paid Mai “a lot” to overcame the usual rules.
By making direct contact with the Mai and keeping the date off books Mr. G skirted the escort company rules, which would include a fine for the girl and a sanction against the customer. With a private confidential arrangement Mai made more money, Mr. G got what he wanted, and the company had plausible deniability with a good result, so it was a win all around. Until now.
(The escort union girls, as a group, really held the power in this arrangement. As a group they simply did not want to deal with some acts, and they could make their rules stick. The escort’s believed that if something wasn’t allowed then nobody would ask for it, so they never had to say “no” to a client.)
A note on an old file (more than 5 years old, pre-Mai) said the Mr. G was good for twice a night, and was not “demanding” in terms of oral sex.
Wednesday afternoon my husband bit the bullet and called Mr. G to see if he could get more insight. The two men got along well, Mr. G understood Tracy’s situation trying to arrange a booking. He would not get specific but asked only for an escort who did “what Mia did last year.” He said that “the rule book was out, but the pay would correspond to what Mai was very happy with.”
Mr. G recognized that Tracy could not arrange something last minute on his own without more details, so he had a counter-proposal. He asked Tracy to give him a name and phone number by close-of-business Wednesday so Mr. G could negotiate his own arrangement for his Thursday night. He was confident he could negotiate a deal that “kept the girl happy” while keeping is own night activities private. However, Mr. G made it clear that if Tracy could not provide somebody to negotiate with, Mr. G would regretfully cancel the visit and seek another supplier “where the services might be more flexible.”
Tracy knew that a firm in Cleveland was trying to break into the Mr. G’s narrow business needs. Also there were rumors that a California-Nevada firm that was making some inroads with using “more flexible girls” in the state where prostitution was legal. There was also talk of “offshore work” where a boat was chartered to avoid state laws. It was greater expense, but with broader services. Mr. G knew all the players, including some new outfits that were trying to break into the market.
Mr. G was older than 55, he said the escort’s age and figure were not great concern, as long as she had the right attitude and was reasonable. Mr. G agreed that an oral warmup was “pleasant enough,” but he saw no benefit “throating.” He also noted that “none of his escorts have complained over morning coffee.”
Tracy said that, hypothetically, a girl might want to negotiate with a little more information about the “input” she was dealing with. Mr. G chuckled and conceded that he was open to such a negotiation in private, after a NDA (Non Disclosure Agreement). Well, that got Mr. G to town and was really the best Tracy could expect.
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