Shifting Gears Ch. 10-11

Chapter 10 -- Scheduling Snafu

I watched Kevin closely to be sure he wasn't having any misgivings about having gone to Jake's swinger party.

Jake called and asked me on a date, too. I told him I wanted to go to the beach, and that's what we did. We drove up the long barrier island almost to the end, where very few people go. I'd made a picnic lunch and we lugged that and all our blankets, lotions, and everything else with us to near the water's edge.

Jake had driven his Hummer. I suspected he could have driven us all the way to where we set up camp for a few hours. I teased him about it. We set up umbrellas for shade, and then did our picnic complete with beer and wine. I went topless since there were so few people around. If anybody noticed other than Jake, I'd be surprised.

We went swimming, listened to the radio and talked about music. I learned he was an accomplished jazz pianist. I begged to hear him play some time soon. We walked about mile down the beach and back, collected six sand dollars as we went; one of them was rare and about six inches across. We wrapped them carefully and put them in the picnic basket. I treasure them to this day.

In late afternoon, we packed up and went back to my apartment. We took showers but at my suggestion we remained naked. That led directly to a lovemaking session that lasted almost two hours and resulted in another shower. I resolved to find an apartment with a shower that could accommodate at least two people.

At my suggestion we went to Gecko's for dinner. I thought it was one of those restaurants where you really got value for money as well a great service. It was local chain. Our whole meal for the two of us, with wine and the tip, cost fifty dollars. Jake obviously liked that. I asked whether he could pay in cryptocurrency, but all he did was laugh and put his Visa card on the bill. I had offered to pay, but he reminded me that I'd done lunch.

I learned later, after a particular situation occurred, that the word 'snafu' was a World War II contraction for 'Situation Normal, All Fucked Up'. I created a 'snafu' situation for myself that ultimately turned out better than all right, but there were three unhappy people for a short time.

The snafu started when I invited Owen to dinner at my apartment. He showed up early and helped me prepare a salad as I worked on the veal parmigiana. Dinner was in front of my living room window with candles on the table, some nice red wine, and soft music.

Our conversation was vibrant and somewhat sexual. The longer we talked, the hornier I got. He told me about some of the romantic and sexual encounters he'd had since college, and if that was his goal, he had an eager participant on his hands.

We quickly shuttled the remains from dinner into the kitchen and stored the leftovers for a later meal.

Back in the living room, I did a little strip tease for Owen as he told me how hot I was, and how he wanted to see my porn video and even watch me enticing some dirty-old men on some stripper stage.

I took his clothes off, and dove onto his cock, taking him all the way into my throat -- a primary skill that Sheri had taught me as crucial to my upbringing.

Owen shifted us as he got near and ate me to two orgasms. He was really good at cunnilingus, especially when it came to my body. He also knew how to drive his fingers into my cunt and rapidly stroke my G-spot in just the right way to make me orgasm and have really horny feelings for him.

We started to fuck with me riding Owen as he lay back on my sofa. We were about ten long, slow strokes of my vagina up and down his long cock when my front door opened and Kevin walked in.

My brain short-circuited. I looked at him in disbelief. "KEVIN!"

He looked at me in disbelief. "BRIE!"

Owen twisted around under me to look to where Kevin stood. He said quietly, "Hi, Kevin. Are you expected?"

To my surprise, I was speechless and Kevin answered Owen's question.

"I thought I was expected," Kevin said. "I had that long drive to our client site today, and I just got back. Brie had said to stop by. We know each other well, so I always just try the door instead of knocking. It was open... obviously."

I rose up and then slid down Owen's cock again. He was still hard. I was still horny, although I now had a dilemma on my hands.

I mumbled, "I forgot that I'd invited Owen for dinner. You already know that I fuck all my dates." I glanced down my nude body to where Owen and I were intimately connected.

Kevin nodded and grinned, "I do. I like that about you. I'll see you tomorrow."

He took a step towards the door when both Owen and I said in unison, "Wait! Don't go."

Kevin stopped and turned back to us with a questioning look. I nudged Owen to speak.

Owen said, "Stay and we'll both make love to Brie."

I added, "I haven't been DPed for a while. I'd like that."

Kevin added, "I don't mind sloppy seconds either."

I'd never heard that term before: sloppy seconds. I figured out what it meant quickly. Owen obviously knew the reference, and so did Kevin. Owen started to piston into my velvety snug love tunnel. I was in ecstasy.

Kevin stripped down at my request, and then I got him nearby so I could suck on his cock as he watched Owen and me moving together, his cock sliding in and out of my vagina. He got very hard, very fast. I had the feeling he liked this kind of thing; I sure did. We were voyeurs.

Owen and Kevin changed places, so I was on my back on the sofa with Kevin fucking me while I sucked on Owen. Kevin and Owen had an aside, and then they both had their orgasms; Kevin deposited inside me, and Owen splattered across my face. I loved it.

Both men cleaned up their messes, but I went off for a moment to the bathroom to complete the job. I also put in a butt plug. I had plans.

My plans went well, too. By the end of the evening, my two lovers were empty of cum, both men had cum in my ass not to mention my other orifices, and I was sexually sated.

I had planned on inviting Owen to stay over, but I thought that would be a slight to Kevin, so around midnight, the two men kissed me goodnight and left. I slept in the wet spot in my own bed.

Well, that snafu worked out well. The truth was that I had never been DPed before that night, although I'd been with two men at the same time. I'd been spit-roasted, but DPing was new. I liked it and had about a dozen orgasms plus all the other good feelings from our lewd act.

To my surprise, Jake asked me out again about a week before his next party. This time we went to the art museum to see a unique exhibition of Chinese art that went back over five thousand years. The museum visit turned out to be more than that, so I was glad that I'd dressed to the nines for him.

As it turned out, since he didn't tell me, he'd donated a million dollars to the museum, and the exhibition was a private grand opening to honor his donation. We were guests of honor, and were also hosted at the accompanying gala dinner in the five-star museum restaurant. Jake even made a few remarks to the two hundred other people -- other donors --about the importance of arts in the history of mankind. He was a spectacular and polished speaker. I was in most of the photographs that got taken of the event, and later appeared in the newspaper that documented the event and his monumental donation.

Kevin found me at work two days later with a copy of one of the news articles and photo. He laid it down on my cubicle desk, and said, "Wow! I can't compete with that."

I laughed. "Kevin, it's not a competition. Jake is good friend as you know. You know him almost as well as I do... well, except you guys don't fuck."

He laughed, too. "Touché. I just want to constantly vie for your affection, but... that is too much." He pointed at the article in the society section of the newspaper.

I replied, "I may not see Jake for two months now, except maybe at his party next Saturday. I've been to one of his parties and never saw him, so the possibility is there."

Sheri came around the corner with the same news article. She put the picture and article on my desk with Kevin's. "For your scrapbook." She was grinning.

I stated, "Kevin can't compete with that."

Sheri looked puzzled at Kevin. "Why would you even want to try? Jake does outrageous things sometimes. He's been lucky in his business, so some of those things are expensive. We all love him though."

Kevin nodded, "I do like the guy."

Sheri said, "And you're not out for his money and he knows that."

Kevin asked, "Is that why he likes us?"

"He knows we're not gold diggers. He went on a date with Brie a couple of months ago, and she took him to the beach and then an inexpensive dinner. She also never mentioned his work or money. He told me a week or so later that he was testing her and that she passed with flying colors, especially when she offered to go Dutch-treat for dinner. He knew her genuine motivations did not include his bank account."

Kevin said, "All that money put him in a difficult situation. He doesn't know whether people like him for his money or just for his personality."

I teased, "He a great lover, too."

Sheri nodded and laughed.

Kevin remarked in a sarcastic tone, "As I said, I can't compete."

Jake became a regular in the society pages of the newspaper, each time with another knock-out female on his arm. Some of those appearances included Maryann, Sheri, Marsha, Sarah, and me. He quickly got a reputation as the area's most eligible bachelor. The social grapevine also heard about his prowess in the bedroom, and that further enhanced his reputation and the invitations to great events.

I went to another gala with Jake, this time because he'd completely funded the renovation and re-equipping of a large building at the local college. There were rumors that a number of co-eds had also graced his bed because of the deal. I was to help defuse that rumor, and acted loving and supportive of the man over the evening.

Jake donated to other causes in the area, especially as he kept accumulating large amounts of money from his trading in cryptocurrencies. I became his date of choice for those events because I dressed just right and always said just the right thing to the other people there. Maryann also got put in the same category.

Sheri and Maryann had spent hours with me talking about how to behave at the kind of charitable galas that Jake was escorting me to. How was I to look? What makeup did I need? What was I to talk about with the Mayor, the head of the institution, the various deans or doctors or curators or whatever of the places he'd donated to? Should I expect any follow-up?

For each event, I did my homework about the institution and their need for money. In the limousine on the way to most events, I was able to give Jake a briefing about the place and how his money was going to make a difference to the people they supported. He was pleasantly surprised at my helpful knowledge.

I didn't realize that my meeting lots of important people through Jake would result in my own star rising. I was embarrassed at a hospital event when Jake and I were introduced together as the donors to the new pediatric wing. I'd given a hundred dollars, but Jake had kicked in thirty million. I blushed and apologized to Jake later. All he did was laugh and kiss me. We made love in the limousine as it drove around after the recognition dinner.

While I was Jake's go-to girl for his important dinners, Maryann became his go-to girl for weekend dates at the various clubs around town. A few times, I'd triple date with Luke and Owen and Sheri, so we were all seen together. The press knew there was no animosity between me and Maryann, but they sold a few newspapers speculating that there was. The two of us put that to rest by appearing at the society editor's desk and ripping him a new asshole the day after the article appeared. The next day there was a retraction. The fourth estate didn't mess with Jake's girlfriends after that.

Through the months of those events, the areas I got coached and advised on by Sheri and Maryann became fewer and fewer. Sheri finally told me one day that I was 'done'.

"I have no more advice to offer you other than on any particular situation, just as I would with anybody. Brie, you're done. I can't see anywhere in life that you need mentoring."

I hugged and kissed and thanked Sheri and then Maryann for all the time they'd spent developing my social and sexual IQ. I was the happiest I'd ever been, and had a whole new kit of coping tools and techniques thanks to them and their tutoring.

I bought each of them some sapphire earrings that I presented to them over a girls' night out dinner. I was teary as I gave a little speech talking about my 'before' and my 'after' to them. We were all happy but crying when I finished praising them.

Our threesome suffered an unusual blow a week later, a day before one of Jake's monthly sex parties. Jake proposed marriage to Maryann. They were at a high-end restaurant named Michael's, and she fainted.

Jake, the maître d', and a waitress revived her and made sure she was all right. Jake reported that with tears of love and affection streaming down her cheeks, Maryann accepted. Jake put a twelve-carat pear-shaped diamond ring on her fingers and kissed her in public. She learned later that Jake had paid just under a million dollars for the ring. The ring was custom designed for him by Harry Winston of New York.

The next night at Jake's sex party both Jake and Maryann fucked everybody in sight. Everybody congratulated them and then wanted to fuck one or the other of them. I was in line to fuck Jake. We laughed at the audacity of what was happening. I also teased Maryann that I'd fucked her fiancé and intended to do it again. She made me promise I would.

The following weekend, ten of us went out on Jake's large yacht. Also present but not participating in our sexual romps was one of Jake's bodyguards. In a low-key conversation with Jake, I also learned that the boat had been weaponized and could wipe out a small flotilla of pirates in the Gulf. He'd also been schooled in the weapons and some martial arts for his own self-preservation and to prevent ransom situations.

Jake and the four other men formed the nucleus of his inner circle: Luke, Owen, Sean, and, to my surprise, Kevin. Their female counterparts were his fiancée Maryann, Sheri, Marsha, Sarah, and me. Whenever we were out and partying in public, the pictures that would appear in the paper always include some or all of us.

More frequently than his monthly parties, the ten of us often got together for, of all things, sexual relations. We all loved to fuck... and suck, and lick and bite and kiss and touch... and any other sexual thing you could think of. We were good at it, and always wanted more.

We ladies got increasingly friendly, and usually were sexually involved with each other while the men rested after some serious exertion. We really liked 'performing' for the men, putting on little lesbo sex shows for them. The men never played together, but they would touch each other when there was a female involved. A few would even join in fellatio on a man if a woman was also involved.

Owen spent increasing amounts of time with me. Owen quit his job at Retail Software Systems, and started his own company building sophisticated technology architectures for companies and what he called 'white hat' hacking and network security."

Since I was able to code and use developer tools to build websites, we often talked shop, but that side of his business suffered because of demand for the network security solutions. One day he told me that he planned to just stop offering to develop the fancy websites.

In an uncharacteristically bold move for me, I told him not to turn down that business; I wanted that work. Almost on a whim, I quit my marketing job at Knightsbridge after talking to all my friends, and became an independent contractor. Right then, my sole business was with Owen's clients, but that soon started to change.

I called my business Porter Consulting in order to have a more professional sounding business that appeared to have more depth than it really did. I even did a fancy and somewhat ostentatious website.

I was quickly booked out for work including some contract work from my old company -- Knightsbridge Manufacturing. Somehow, Kevin, Sheri, Marsha, and Sarah thought that I was the only person that could do their marketing website work, so I got a lot of sole source work. That made up about a quarter of my work hours. Other clients found me for both market planning and website work, and soon I had a thriving business.

Owen and I were constantly cross-referring each other for work. It was just so normal. I felt so good when one of my clients would use him for work. He told me the feeling was mutual.

Chapter 11 - Freelancers

Owen and I didn't have offices. It was either my living room or his. He had the nicer apartment, so we worked there more often than not. I could work anyplace with the Internet, my laptop, and a cellphone.

Owen started to travel to increasingly distant clients, and just for fun I started to tag along. I'd never traveled more than a few miles from my home town when younger. We'd be in some great city, I'd work in the hotel while he went to the client site, and then we'd prowl around as tourists that evening and the next day. If we could plan the trip right, sometimes we could get a whole weekend in a remote city.

We were in Denver for two work days and a weekend, when Owen got invited to have Thursday evening dinner with the client and his wife. Owen quickly explained that his girlfriend was along for the trip, and I got included in the invitation.

I went through the meager wardrobe that I'd brought on the trip. If I thought we'd have overnights where we could have some fun, I'd bring one of my slinky cocktail dresses and my CFM shoes. My daytime attire when working at the hotel consisted of sexy jeans and usually a crop top, with flip-flops.

I put on the sexy cocktail dress for our dinner. It was one of those that had two-inch freeboard between the hemline and my pussy lips. Also, I hadn't brought any underwear. I liked going without a bra, and Owen liked that, as well as when I went without any undies, so there I was ready for a social evening in sexy shoes, a sexy dress, and no undies.

Owen gave me a quick inspection, approved of everything he saw, kissed me, and we raced downstairs and got an Uber to his client's house in the Washington Park part of the city -- a very urban brick home on a busy street with a beautiful public park and pond across the street.

Mike and Grace welcomed us into their home with smiles and polite hugs. Owen had managed to get two bottles of wine from the concierge at the hotel, so we weren't arriving for dinner empty handed.

Mike and Owen were wearing slacks and sport shirts, and looked very professional. Grace had the remnants of a business suit on from her day of work teaching at the University of Denver. I blushed because I was so overdressed for a casual family dinner. I sighed and when Mike asked, I accepted his offer by requesting a Manhattan.

Grace disappeared and came back ten minutes later in CFM shoes and a very short cocktail dress. She'd also added some sexy eye shadow, eyeliner, and high gloss lipstick to her look.

Grace grinned at me. "I couldn't let you be alone, and I never get to dress up like this except when we travel out of the city somewhere. I can't afford to be seen and have my purist academic reputation besmirched." She giggled.

I bowed and toasted her with my drink. She picked up hers and we clinked glasses. As the men talked about something, she said to me, "Usually when I wear this, I don't wear underwear."