Part 1

Chapter 0. Preview And Background

I loved being under Roger’s body again, panting in passion as he fucked his cock deep into me, stroking again and again.

I pulled his lips to mine so we could share the taste of my sex juices on Roger’s lips and tongue - he always eats me first. I also caught a lingering trace of my husband’s cum on Roger’s tongue, my husband had fucked me ‘for luck’ before I left the house for this date. Roger knew that, but he was heroic as he boldly dove in to eat my creampie pussy as soon as we were in bed.

Now Roger was hammering his cock into me like a champion porno stud. It was even better than our first intimate date after a decade (“First Date As A Whore”). That was 9 weeks ago when I blindsided him, walking into his hotel room I suddenly exposed my naked body and posed myself on his bed. That night he expected a normal social date with a couple of old college friends, including dinner with a few drinks at a club like last year and the year before, then us passing him off a young hardbody professional escort 5 to 10 years younger than me. In this town escorts are a union job with high standards. He would enjoy the night with her while he dreamed of doing me. But the way I slipped into the role as his ‘whore du jour’ was a complete surprise. I revealed it to him along with my shocking lack of undergarments. He got the message.

That night with my body was his surprise treat and he treated me wonderfully.

Roger, my husband Tracy and I shared dozens of normal social/business dates, having a good time together. Usually my husband’s company provided an escort for him to enjoy before his quarterly business meeting in Tracy’s office. But on Roger’s last visit I explained that, due to circumstances beyond our control, I was eagerly subbing for Roger’s usual overnight entertainment. I did so with my husband’s encouragement. As a bonus, because we were all good friends who played naked in college, I expected to offer some ‘off the menu’ specials that the normal union escorts could not provide. Things like accepting passionate kisses at both ends.

We both enjoyed an active night, and my husband enjoyed reenacting it with me afterward. Now we were going to expand things. We planned this Thursday night as the start of a threesome weekend.

After the Friday office meeting my husband would ‘take Roger to the airport’ as usual. The difference was that instead of boarding a plane, Roger would exchange his tickets for a Monday flight so he could be our guest for the weekend. The plan was for me to go back and forth between adjacent beds, sexhausting each lover as the other watched. Yum! I was also looking forward to a DP Saturday. Basically, the plan was for me to be totally fucked by them both. Yum Yum!

Why were we doing this? My payoff for this plan was going to be a lot of very good feelings. Roger’s payoff was getting to enjoy me, something he really missed in the decade since he graduated college. My husband was happy to see my pleased, plus he hoped to catch a nasty business saboteur his firm had code-named “Gaga.” Finally, Roger’s enhanced order would secure both men a promotion at their respective firms, making it a big win for all.

Background

(Skip this seven paragraph section if you read the earlier stories.)

I met my guy at high school freshman orientation, based on the unlikely name that we, a boy and a girl, had both been given at birth: Tracy Ronnie Maier. When we met there was an instant attraction, we ‘got’ each other. At the time we knew of no common relatives, but eventually we learned that we were in fact distant cousins, our fathers had a paternal grandfather (Maier) in common. In most states second cousins can marry, and we considered it. But for us there was another issue. My late maternal grandfather’s will leaves tens of millions of dollars to me, in two bequests, at the ages of 35 and 42. However, if I marry before those dates my greedy uncles (my mother’s brothers) agreed to abuse a provision in the will to cheat me out of my share, splitting the funds with their own lazy lay-about offspring. So effectively, I cannot marry without losing a fortune.

In college we made special friends with Roger and his girl Foxxy. Roger witnessed the end of the coupling where my man and I gave our virginity to each other. On weekends the two couples adding same room soft-sex swaps, for thrills to inspire the guys to “one more time.” Roger graduated after our first year, but we three remained friends. After college Tracy and I could not marry, but our love grew so we lived as husband and wife. There was even a ceremony, a barn wedding for friends and relatives. But instead of signing the marriage paperwork after the ceremony, my man and I opted to exercise an ambiguity (since corrected) in state law to legally file as opposite-sex domestic partners. We refer to each other as husband and wife. Only our parents and the State of Wisconsin know the truth. BTW, Wisconsin does not recognize common law marriages established after 1917.

I love my husband dearly, and up until my recent ‘escort’ date with Roger I had been faithful. But I dreamed about those Sunday nights in college when we soft-swapped. I felt a special thrill when my man watched Roger attending to my breasts or my pussy, and I know how watching aroused both guys. I confessed that over the last decade I sometimes lusted for Roger’s body, which is so different from my husband. My husband knows about my fantasies and has always encouraged them. After graduation my husband’s job (in sales) reacquainted him with Roger (who was a buyer) and so we shared social dates of dinner and dancing when he visited on business four times a year. On those dates sometimes Roger and I danced into dark corners where lips and fingers can wander for extra thrills. My husband does not object because I am always much hotter for him in bed afterward.

This year a “Joker+Gaga” problem disrupted my husband’s job. My husband’s firm contracts escorts for visiting customers, we are a small town and transportation is difficult so the Chamber of Commerce winks at the girls to try and level the field. But somebody was blocking, actively keeping my husband from getting his escorts for selected customers. On my first date I volunteered to play the ‘overnight escort’ who would get naked and put out for Roger in his hotel bed. It was my hubby’s idea, since college I had lusted for Roger so I was not hard to convince. For Roger, finally screwing me was a dream come true and a lot of fun for all. My second date was a legitimate emergency when the escort for a big customer accepted a last minute wedding proposal. That did not sound like as much fun as my old friend, but it turned out to be enjoyable and paid off when we learned the “Joker” was somebody within the company who wanted my husband’s job. We learned his name, but it was clear he had a local associate we called “Gaga.” The COO could not move against Joker until we also knew who his local contact was. The company wanted Gaga identified before the December rush of sales meetings, so my husband and Roger came up with a trap. I was the bait, and we all decided to make it a threesome fucking weekend of it as a bonus.

Since college I have had a fantasy of going back and forth, between Roger and Tracy. The guys also wanted to try a Double Penetration with me, which sounded too good to be true.

I am a pilot with my own plane, a Piper Comanche formerly owned by my parents. It was a sort of a post-graduation-from-colege gift from them. They were airplane owners as well as swingers, for them the two often went together. As teens they actually met in a hanger, and when they married they spent their honeymoon in Oshkosh at the EAA. Early when I was in high school and showed an interest in flying they made a long-term deal with me. If I 1) learned to fly, 2) graduated from college within 5 years (I did a business and tax degree in 3.5 years), and 3) worked in a related career for two years with a gross pay that exceeded my total college cost, they would give me their Comanche as a “mission accomplished” gift. This clever incentive agreement kept me on the path and working towards a real career (as a tax accountant) instead of getting established in a useless college degree path as so many do. The deal reflected the same type of thinking as my grandfather’s will, but without the greedy uncles.

Our written deal did not specify full-time work, we discussed options based on gross pay which my parents were focused on. I had spotted a shortcut for their third requirement. In my research I discovered that tax work includes a LOT of overtime in the tax season (the worst time of the year for Wisconsin weather), plus the year-end bonus is heavily weighted toward overtime. However, tax specialists, even those without a CPA (which requires a fifth year and then passing a tough exam), can earn a healthy full-time annual salary based on overtime in this critical three-month tax period. That was one of my considerations in college. Flying is an expensive hobby, but tax work pays well enough so I could take the rest of the year off and still cover my flying costs. Also, once I inherit millions from my grandfather I will have to know about taxes, so I get a double benefit for the rest of my life.

Chapter 1. Setting A Trap For Gaga

A decade after college, the unusual Joker situation prompted my husband to arrange for me to spend a night ‘acting as an escort’ for Roger, with all the usual overnight activities. I was willing, Roger was very pleasantly surprised, and all three of us were more than happy with the outcome. That night also crystalized some self-evaluation for all three of us. After that night the three of us talked more frequently, we all felt closer. We were coming up on a busy time for all of us, but we knew that in the future there would be more sex between me and Roger.

Talking with me during our night together, Roger realized that he had sacrificed his personal happiness for his dedication to his family business. Being with me for the night made him realize that he needed to re-order his priorities, including a job change, a physical move from New York, and opening himself to the possibility of love. (Roger was a marine before starting college, he is now on the wrong side of 35 and because of his job he has never had a lasting relationship. My man and I are both 29.) A series of recent inheritances of shares in the family firm gave him the push he needed. Roger was soon to leave his current job to take a seat as a member of the Board.

I was still 7 years from receiving my life-changing inheritance, so my husband and I were both tied economically to the community where he had a full time career and I had my tax clientele. We loved each other more than ever. We both realized that I also carried a lust for Roger, and I loved my husband even more because he eagerly sanctioned the occasional exercise of that lust. He insisted that he would like it even more if he could enjoy my affair first hand, “like in college.” I made some new friendships that also suggested paths to new excitements, like my friendship with Ariel, a virgin I met on my second date as an escort. Ariel was also a pilot so we had already made plans for a “fly-in camping date” during the next EAA meeting in Oshkosh. She also talked about me helping her with “her virginity issue” sometime.

My husband had attained a significant step in his job, it was the last “up or out” year on his career track which was part of why Joker picked him to attack. If the Joker and his associate are not stopped soon, they would undercut his current year successes and could even derail his career permanently. After my two escort dates Tracy loves me even more, and after reliving my joy after my night with Roger, he realized that my happiness and his would increase if we indulged a few opportunities for more safe sexual adventurers. He viewed that as a positive change. (However, my becoming a full-time escort was NOT part of our plans.)

After my second date with Mr. G and his sons we now knew who the Joker was, he was somebody the California office with access to the firm’s systems who got the information about the “who and when” from my husband’s appointment list. The Joker was aided by a local associate we code-named “Gaga.” Perhaps they worked for the company, or the firm that managed the girls, or possibly it was somebody outside the loop with another connection, like the car service or a beautician for the escorts. With December being the most significant month for the business, we had to identify Gaga soon or they might torpedo my husband’s career even at this late stage.

At one point in the general conversation between the three of us, Roger made a comment about playing offense instead of defense. Tracy was a safety in college, a defensive player who always reacted. But Roger was a marine, who was trained to think in terms of attacking with innovation. Together they came up with a play to trap all the Gaga(s). So for the third time I slipped into the scandalous minimal but fashionable threads of a professional escort to stroll the path of a whore into a pricy hotel with eager intimate intent for a man who was not my husband. Just like that the idea of spending a whole weekend with BOTH guys, passing my naked well-fucked body back and forth while watching the festivities, leapt to mind. I felt myself get wet. I said, “You boys plan the details of your trap. Meanwhile I will dream of a weekend which will be like a ‘Greatest Hits’ collection of our weekends from college. Without Foxxy around I guess I will (blush) have to do double duty. I imagine I will want three times my normal weekend demands. Good thing I am approaching my sexual peak as a woman.” (I read that somewhere.)

The play would need an established buyer (Roger) with a tempting large order, and an escort (me playing ‘Evie the escort’ again) that my husband could call in desperation at the last minute. Because I was still on probation as an escort, I was not on the firm’s regular list of escorts so I was essentially invisible to most people in the business. If Gaga had my name, it would be from the payment list or some other internal source, so she would expose herself if she tried to stop me.

Roger was always scheduled for his 4th quarter sales visit to my husband on the second Friday in December. My husband’s plan was to move the meeting up a month, to the sales lull of mid-November. Both men would do everything they normally did setting up the meeting and the escort, but this time corporate investigators and PIs would be watching everybody who was part of the business, like the hotel clerks, the escort company staff, and even those within the company.