Third Date as a Whore - Friday - Cover

Third Date as a Whore - Friday

Copyright© 2026 by LolaPaul

Chapter 1. The Gift (no sex)

Erotica Sex Story: Chapter 1. The Gift (no sex) - My third date as a whore was with Roger, our soft-swap buddy from college. I loved my husband but he knew I lusted for Roger. My guy loved me enough to stretch this overnight date to the weekend, with both men each taking their turns pleasuring my body while the other watched. The Friday evening started late, but damn, I got what I wanted from both. It ended with something sinfully naughty.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Sharing   Slut Wife   Wife Watching   Swinging   Cream Pie   Tit-Fucking  

His POV

At Tracy’s Office

When Roger got to my office Friday morning we were both in a very good mood and all was going as planned. Roger had spent the night enjoying his cock in my woman’s mouth, pussy and ass. She told me she had a great night serving our dear college friend, and was looking forward to “twice as much fun” this weekend.

Roger concurred with my wife, he was very pleased after his overnight adventuers. Now we had to do our jobs, negotiating purchase contracts. We would finish our jobs with Roger’s seeming departure for New York. Then we would start the weekend fun for all three of us.

My 4th quarter sales meeting with Roger is normally scheduled in December, but we moved it up a month to trap some people we called “the Joker and Gaga” who were trying to sabotage either me or my employer. Roger was helping us trap the Joker’s accomplices, and since he was here we decided to have him join us for the weekend.

Roger and I planned to be together all day, even lunch break at the deli included negotiation, but it was all friendlier and more relaxed than usual. We were both looking at job changes and promotions on January 1, so we expected this to be our last meeting in these roles. In addition to his usual seasonal business Roger was bringing a new order, replacing one of his other suppliers by taking one of our standard lines and running a few minor changes. Our business is competitive so stealing an order was a big deal for my firm.

Our job as negotiators really is as intermediaries with our own production people. They talked to us and we talked to each other, in general production folks tend to get too emotional about their positions so they need a go-between. Our job was to facilitate communication.

As always the hangup was price, and that in turn depends on how often we had to change each line, some of which served many different customers. The new order, a steal or interception from a rival firm, was highly prized by top management. But our operating folks saw it as a disruption to their smooth routine so they always raised a lot of issues. For this new order Roger’s people wanted 12 shipments, on the 3rd of each month, and stressed they had to be on time. But 12 setups carried a steep price in terms of disrupting production for my other customers. My production people hated it. My people claimed 6 production runs a year, with setups and downtime between other jobs, was good for them. But nobody wanted to carry the excess inventory and Roger’s people needed more frequent opportunities to make seasonal adjustments. Also, the product had a short shelf life. Roger said his people needed the once-a-month shipping because they had no room to store more input.

It was always like this, between us we kidded about the operations folks we worked with. He called his operations folks. I called my operations folks. People on the phones were driven to extremes by imagined trivial horrors messing up their sacred production schedule. Roger and I stayed cool and friendly. In between calls we shared some of last night’s video showing him screwing my happy wife every way but loose, and talking about the coming weekend’s festivities when we planned to share her body some more. We were all looking forward to repeatedly draining our balls.

Around 3 in the afternoon Roger’s COO started to push his inventory folks, pointing out that their current supplier was never on time which always killed their schedules, made them work overtime on weekends, caused cost overruns. The Board was tired of the lost profits so they should settle for the win and fix the problems. My COO wanted the order so he laid down the law that if we didn’t solve our differences today, the production higher-ups had to come in Saturday to finish the talks. However, he was not paying for a weekend escort for Roger. To avoid the threat both sets of production people finally gave us the wiggle room for the compromise we all knew was coming.

By 4:05 we signed the deal giving Roger 8 production runs a year for the new order, 2 each quarter - we had the firm dates starting next January 3. My production folks would produce excess product each run, then store the excess and ship from inventory as needed. My production people had to guarantee the quality of the production in inventory, if there was a problem they would have to interrupt their current ops and incur overtime charges, but that was part of the deal and the line manager either had to make it work or the COO would find somebody else. Roger’s people got a better deal then their previous supplier ever actually delivered. My production droids had the whole weekend off so they did not feel compelled to slash my tires. (I checked to make sure, they were known to jump the gun, especially on Packer/Badger weekends - which this was. They all know my car.)

When I called in the deal my COO was a happy man, he said I should take Roger to “the steak place” - just the two of us, no dates - on his corporate dime. Also, because this counted as another interception for me (from Cleveland this time), he had already signed my promotion paperwork, effective Monday. That was 7 weeks early! I would finish the year in my present position but at the higher pay rate. My actual new position was still subject to discussion based on who retired, other transfers, etc. My current boss was worried I might push him into semi-retirement, but to be honest I really did not want his job. I was already making notes on dividing up my present clients, I expected to take some of the load supervising other people.

I knew my COO got an annual bonus for each interception, which was doubled if it was a order from rivals in Cleveland or New Jersey, so I got the feeling I could write my own ticket for my next move.

At the airport I dropped Roger at the Departure gate in time for his flight - which he would not be taking. That was the last step in our trap, we figured some Gaga might watch the departures gate. At the counter Roger changed his tickets to a Monday morning flight eventually taking him to Jacksonville Florida for two more weeks of vacation. In the rest room he added a wig, glasses and reversed his coat before he came out the Arrivals gate where I was waiting. Roger’s trip to the airline’s counter was important because the last Gaga in the chain might get a report my arrival at the airport with Roger, dropping him off at the ticket counter. We figured that might be the final piece of chain that triggered the release of the funds that Joker paid his helpers. (That is how I’d do it, we figured sabotage job cost Joker $3,000.) We were following the money so that payment would provide the last piece of evidence in the puzzle and send somebody to jail. Now professional investigators would do their thing to find any of the Joker’s associates that might be out there.

This all started when somebody we called Joker had tried to disrupt my sales operations by blocking the escorts I scheduled. That was the reason for my wife’s first date as an escort for Roger two months ago. The name of the Joker had already been revealed by Mr. G, after my wife’s second date as an escort for him. Joker was salesman in our California/Nevada office who was part of a fraud scheme. We knew that the Joker had one or more local accomplices we called “Gagas.” I suggested moving up Roger’s usual December trip to mid-November and using that to trap all the troublemakers.

As a sales meeting Roger’s visit was 100% legitimate and, with the interception it was more successful than expected. But because Roger, my wife and I were friends of a special sort, we decided that we would make this an extended weekend visits with benefits. When Roger got back into my car he had his ticket leaving Monday morning and we were both looking forward to the weekend playing with my wife.

I knew my wife was super excited about the prospect of doing both of us in sequence. We had played these games in college and we talked about these fantasies since Roger graduated. As I drove we talked about him being with my wife in the future. We were unlikely to see each other for sales meetings in the future, we were both in the air about what jobs we would have in three months.

Since renewing her lustful connection with Roger, my wife had open the possibility of more frequent sex visits with him. Now that business was over and it was just the two of us, Roger asked if I was really okay about him visiting my wife either here or “someplace they might both travel to,” possibly without me. As a couple we had talked about this idea over the past few weeks, but this was our first guy-to-guy discussion of him taking a sex vacation with my wife. However, after setting Roger up for two overnights with my wife at the hotel it was pretty clear that I was okay with it. Now he wanted to be clear on the details. His said his first thought was a 4 to 6 days around Valentine’s day in the Bahamas.

I mentioned that in general that was fine with me, but mid-February would not do, she worked overtime (80 hours a week) during tax season from mid-January until mid-April. But the rest of the year we all agreed that visits were okay, especially during my busy periods.

After her tax season my first thoughts were for sex-stopovers for the two of them might be adding a weekend to his periodic visits to cities like St. Paul or Fargo. She had the same ideas. Those cities did not provide the escorts we did, so for him they were lonely trips. In Fargo sex is pretty much the only thing to do with spare time.

For longer visits we both talked about her flying to some ‘Adults Only’ destinations. She loved to fly (it was the reason for her tax job) and her Piper Comanche had the range to reach some adult spots on the coast. Also, for a flight over water, like the Bahamas or St. Croix, she could borrow her parents twin-engine Piper Seminole, maybe with me along. When flying over water many pilots like a second engine and a second person in the cockpit. I was not a licensed pilot, but I had some lessons and a few hours of practice in both planes.

I said we discussed some details about short visits, either him visiting here or her traveling to him. Outside of tax season both were possible, if my wife could enjoy being with Roger during a period when I was too busy it was better for all of us. There were times each year when I was too busy with my job to be a good husband. “We will take two weeks together in late April when she needs the break after tax season. The Bahamas and Yucatan are in range but lately she is talking about an adult place near Tampa. I already have my 2-week vacation reserved from April 20 to May 4 but we don’t have a firm destination yet. You would be welcome for that, or maybe a better choice was some overlap, like you joining us on April 28 for two weeks. The rest of the year we are flexible, maybe a long weekend or up to a week someplace. I love her and she loves me, plus I trust you to make her happy, so I am open to her being with you, with or without me.”

Roger had not realized how her tax work was so much overtime. Some of her regular clients needed normal hours, others needed weekends or evenings. Her flexibility was a big advantage. Many of her clients were already scheduled for this year and next year! She left 20% of her busy time unscheduled so she could get a share of the walk-in business, some of those turned into big bucks over time. The CPA firm she worked for operated year-round but they had a good system for the seasonal work dealing with the tax surge. Taxes took place when all their regular guys are overloaded with year-end work. They knew if she went independent she would take her regular clients with her, so the CPA firm kept kept her happy.

At this point Roger and I were both thinking of at least three extended weekends next year where she would join him without me, plus some threesome-time at his house or mine so she could enjoy the attentions of both of us sexing her in turns or together, like this weekend.

After leaving the airport we had plenty of time before our dinner reservations at the steak joint so Roger asked me to stop at a custom jewelry shop in town, it was a “by appointment only” places but he had been in communication with the semi-retired owner about a gift for Tracy. Now he wanted to talk to me about it, just to be sure.

On the way over he stressed that he didn’t want to step on any toes, but he was so very appreciative of their time together he wanted to give my wife “something significant as a lover.” We both knew that she loved me and that she lusted for him. We all liked the result. I didn’t object, I said a gift made sense if she was going to “be his overnight date more often.” I assured him I was okay with it.

When we arrived at the shop the owner showed us a diamond tennis bracelet that Roger had already talked to him about. Roger asked me if it would be appropriate for him to give it to my wife as a sign of his affection. He really felt strongly about this but there were two issue. First he knew in some circles a bracelet (wrist or ankle) was a signal of swingers. Second, he was concerned that diamonds “might send a wrong message from a part-time lover.”

We both knew my wife was not a swinger, she had no interest in being approached by others. But Roger really wanted to give her to something, so he thought of the tennis bracelet and suggested this piece, subject to my sincere approval.

He also wondered if there might be other guys. I assured him that her only other date since college was business-related, when she subbed for Mia Vee. She was not looking for a regular escort job. Her feeling about Roger had been part of our marriage, but the circumstances did not favor them getting together until now. Outside of Roger, no other guys were anticipated. However, she had made a special friend of Mr. G’s daughter Ariel. She was 18 and a virgin but she was looking to change that. They already had plans for a week at EAA in Oshkosh this coming summer.

 
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