Ruby's Business Trip

WARNING: If you don't like stories where the cheater gets away with it or gets forgiven for it, this story and many others in my catalog are not for you. Unless otherwise labeled, my stories are fiction no marriage has been endangered to create this story. This is not our universe though it has similarities. STDs are not an issue in this universe, unless they feature in the story line.

Ruby's Business Trip

I was devastated when my husband served me divorce papers out of the blue. I had no hint that there was a problem in our marriage. I suggested counseling, which he rejected. My lawyer advised that the offered settlement was fair and reasonable, and I should take it. I settled with him without a big fight. I keep the kids, the cat, the house (the mortgage had paid out a few years back) and receive support until the children complete university, or other post-secondary school. Since there was no fight, it was a quick divorce.

I sold the house, and moved to a smaller house across town, walking distance to my parents, so the kids could go there after school, and I started to rebuild my life. That is when I discovered that he had been cheating on me for over a year. It came in the form of a wedding invitation for me and the kids to attend his wedding to his lover. All of a sudden everything made sense, she had shown up about two years before the divorce. She was his new assistant at work, 15 years younger than me. I never suspected anything. I trusted him. I never considered her to be a threat.

My solace was work. My boss gave me paid time off to sort things out, and I repaid him by working extra hard. Six months after the divorce, I received a promotion. I now have more direct customer interactions. It came with a significant increase in pay, but required additional travel. My mother stepped up to handle the child care and while my life was more frantic, it was also more satisfying. Even the kids liked the new regime. My parents became more involved in the kid's lives, and they said they enjoyed it. My ex-husband is almost gone, he sees the kids when I ask him to, or on birthdays and some holidays. Three months after the wedding, she is pregnant. Nine months after the divorce, I have settled into the new routine, and finally start thinking about maybe finding a man to give me the personal attention that I am lacking.

For the first time since I started working for Amadine Industrial, I look at the men in the office with an eye to a potential relationship. Pickings are slim. The only single man is the owner, my boss. He is a couple of decades older than me. He is a "Distinguished Gentleman" which I find very attractive. He is also fit and active. Unusual in a man his age. However, he has made it clear that he does not condone personal relationships within the office, so he is out.

We have done a few trips to visit clients. I provide project management for equipment installations so I get deeply involved with the client's engineering departments. We jointly schedule the necessary infrastructure for the equipment installation, and manage the installation and setup of the equipment.

In October we make a trip half way across the country to a major city to visit a client and get things organized. Brad, my boss has accompanied me, as this is one of the largest installations we have attempted. He put us up in the Crowne Plaza, a 5-star hotel. We are here for two weeks, and the work is grueling. We are at the client office for 8AM and regularly work till late at night. However, Friday comes and we all break for the weekend at 4. Brad says I am on my own for dinner as he has plans. He is meeting a friend.

I am in the lobby bar talking to the bartender about possible dinner places when I spot someone entering the lobby. I look again. It is Donna, my high school BFF. I shout "Donna! Over here."

Donna looks for the unexpected voice, sees me. She looks puzzled. "Ruby?" She heads over to the bar. "Ruby? What are you doing here?"

"I am here for work. Why are you here?"

"Tom got transferred. I am at the hotel to meet a client."

"Anybody I know? What kind of work are you doing?"

She pulls out a piece of paper. "Brad Wilkins. I don't know him. It will be our first meeting."

"Oh my god, he is my boss." I look at her, and revise my assessment of what she is wearing. Throughout high school, Donna was my BFF. She was always sexy and had a lot of boyfriends. I was OK looking and tagged along in her wake, occasionally picked up a discarded boyfriend. I whisper "My god, are you working as an escort? Does Tom know?"

"We ran into financial trouble. This seemed like a solution. I managed to convince Tom that it was his idea. I thought it would be a short-term solution. Then I found that I really like it. More sex than I had since I got married. Not hurt by the fact that the money is really good. I do some work with a national agency. Brad is apparently a regular. It makes the work safer. We pay part of our fee to the agency but have assurance that the client has been screened and is likely to be safe to work for."

"Have you had bad dates?"

"A couple. Tom had to go and deal with one who stole my fees."

"I guess we have a lot of catching up to do, twenty some years I guess." Just then I spot Brad coming out of the elevator. "Brad! Brad! Over here."

"Look, he thinks my name is Serina. We can talk in the morning. He has hired me for tonight."

Brad arrives. "Brad, this is my high school friend Serina. Seems she is your meeting."

Brad's face drops. "Look, this isn't what you think it is."

"Oh Brad, I am pretty sure it is exactly what I think it is, after all, I know Serena."

"Look, can you keep this to yourself, I wouldn't want anyone in the office to find out that I seek out company while I am on the road."

"Absolutely. However, I was sitting here thinking how can I get laid. Would you be interested in making it a threesome?"

Donna smiled.

"No, no way. I will not have a relationship with someone who works for me."

"OK, how about with Angel, an associate of D' ah Serena's?" Almost blew Donna's cover.

Brad paused and looked at me in a bit more detail. "Why don't we three go and have dinner. We can talk in a bit more detail about Angel. That's if it is OK with you Serina?"

"Well, we have shared guys before, so I am game."

Brad looked at me, and then Serina. "You have?"

"Yeah, we were wild at high school."

Donna commented wistfully. "Yeah, those were some wild parties, weren't they."

Brad took Donna's hand, "OK, let's get a cab."

At the restaurant they were able to seat an extra person, so that at least worked out. Brad looks at me. "OK, first Angel and Ruby are two different people. I don't want to see Angel showing up at the office, or anywhere else."

"Understood. That works for me as well. I don't want anyone at the office thinking that Ruby has been screwing her way to the top. I particularly don't want any of them calling for Angel to provide services, or dropping an accidental comment when my mother drops by with the kids."

"What are you charging, Angel?"

"Same as Serena."

"I don't have enough cash for that."

"Understood, however I think your credit is good with me. It seems that Angel knows where you work."

"It won't come to that; I will get the cash tomorrow, or maybe this evening if we see a cash machine." He sat back and looked at the pair of us. "I have thought about hiring a pair for a threesome. It looks like today is the day." He grinned. "If this works out, I might be interested in extending the time till the end of day on Sunday. Assuming that works for you Serena."

"I am available till noon on Sunday, I have another client Sunday afternoon. I assume you would be looking for the weekend rate from my web site?"

"Yes, if that is acceptable."

"Of course."

Brad paused. Then he looked at me. "Angel, have you been tested recently?"

"After my husband left me, I was tested. It seems he had been having a long-term affair before deciding to file for divorce. I figured I should be tested. It was a while ago, but I have not been with anyone since. In fact, this will be the first since my husband served the divorce papers."

"Are you on birth control? Are you comfortable without a condom?"

"I am, what about Serena?"

"I have not seen Brad's latest test results. If he is clean, I am happy. Of course I am on birth control, an IUD."

"Me too."

"My test results are in my room. I am clean."

The dinner was good. Definitely a level above what I would have chosen if I was paying.

On the way back to the hotel, Brad found a cash machine and withdrew the limit, $5,000. Back at the hotel, I found that Brad had chosen a suite for himself. But then he is a frequent visitor at the chain, so he gets free upgrades. I'm not sure how this was going to work. It was 25 years ago when Donna and I had cornered some nerdy guy who's name I cannot remember. However, Donna had a plan, or maybe a script, and I followed along.

"First the STD tests."

Brad opened a folder and handed Serena (must learn to think of her that way to prevent problems) his test results.

Serena looked at the results. "I need ID to show that this is the same person as you."

Brad passed her his driver license and health card. Serena pulled a test results sheet from her purse and hands it to Brad. He looked it over. I noticed that the report had a picture of her on the page.

Serina reviewed his report then handed everything back. "OK, that is good. The night rate is $2,000 each, the weekend rate is $3,500 each."

Brad handed back her test sheet and got out $7,000. He paid us both for the weekend. My share was more than my semi-monthly take home pay. I stuffed it in my purse. Three weekends a month would more than double my income. I will need to talk to an accountant, and maybe a lawyer. Escorting is, at best, only marginally legal.

Serena started unbuttoning Brad's shirt. He started unbuttoning hers. I reach up and undo one of my buttons, then Brad interrupted me. "No, let me do that." I stop and wait, after their shirts were off, Brad turns to me and takes mine off. God, I never realized just how intense it is for you to be undressed by someone else.

Next came bras. Serena is wearing a baby blue frilly silky bra. Mine a more conservative pink bra with a lace edging. Brad took the opportunity to fondle our breasts and suck on each nipple for a moment. Serena is a 38D, and I am a 36C. If I wasn't wet before, there is no doubt that I am wet now. Next, Serena's skirt, my and Brad's pants. Then underpants. Serena's are a frilly thong matching her bra. Brads are jockey shorts. Mine, rather conservative but pink, matching my bra. Serena is shaved or maybe waxed. I have trimmed on the idea that I might try to get laid. Brad is au naturelle.

Serena and I rub his cock, one on either side. He looks to be a good 7 inches, and fairly heavy. I don't know about Serena, but he will be my largest. Brad steps back and flops onto the bed. Serena takes him in her mouth. I climb onto the bed and offer a nipple for Brad to suck on. I am so wet that I can feel a drip starting its way down my leg. Brad switches back and forth between my two nipples.

I watch Serena. She is deep throating Brad, going all the way to the root. I can see her throat bulging at the deepest point in each stroke. I don't think I can do that. Brad stiffens up, grabs her head and pulls it down all the way. I see Serena swallowing, and swallowing. After a minute Brad releases her, she pulls up and gasps for air.

"My god, Serena, I don't think I have ever had anyone go down on me that well." Brad fondles her breasts. Brad moves to fondling my breasts. Serena sits back on the edge of the bed and watches us. Brad rapidly goes soft.

"Yeah, I had to do a lot of practicing on my husband to get that down pat."

"They say you need 10,000 hours of practice to become the best at anything. I envy your husband."

Serena smiled "I think he managed to enjoy his part in the practicing."

We repositioned ourselves on the bed with Brad in the middle. He had an arm around each of us, and I was close enough to Serena that I could stoke her body. Just like the old times. Serena slowly stroked his cock.

We have about 10 minutes of small talk. Serena sits up, I look and she has him stiff again. "OK Brad, what would you like next?" She keeps rubbing his cock.

"How about Angel, you start cowgirl? Then I will tap you off and Serena on."

I sat up and then straddled Brad. I found his cock, and guided it into me. I just about came just from insertion. After all, it has been about a year since I last had sex. I rock back and forth for a bit, then lean forward into what I call the Jockey position, rubbing my nipples along his chest, sliding back and forth. After a bit Brad taps my leg, I roll off, and start playing with my clit. Serena straddled him and quickly moves to rubbing her nipples on his chest. Brad groans. There are two more exchanges before Brad stiffens then drives his load deep into Serena. She rolls off, and I climb over and go down on her, licking the spillage, and then her clit. She must have been close to the line, because she came quickly, spurting out a bunch of cum, which I quickly clean up. Then she rolls me over, and goes down on me. It took me longer to cum, but not a lot longer. I am sure that the next room heard Serena cum, but the whole bloody hotel had to hear me cum.

Next, Brad piles us up with me on top. Both of us in doggy. He switches back and forth between us. This time he finishes in me. God, it feels good. It pushes me over the line and I have a strong orgasm. I can see why Serena likes this as an occupation. Having cum in my pussy feels really good. Serena does cleanup and I cum again. Not as strong as the last one, but still far better than using a dildo or vibrator.

Brad is clearly reaching his limit, so we pull back the covers, and all climb in, then lights out. Turns out that Brad snores a lot. I climb over the snoring Brad, and Serena and I cuddle till sleep comes. At some point in the night, I am woken up when Brad fucks Serena. I get up and go to the bathroom, then return to the other side of Brad. The time is 2:45.

I wake up to Brad's cock rubbing against my pussy in prone position. I spread my legs, and rotate my hips to improve his access. It does not take long till I feel the warmth in my pussy. Brad climbs back into his place in the bed, and throws the covers over me again. Brad is easily 20 years older than my ex-husband, but far more active in the bed than my ex ever was. I check the clock before drifting back to sleep, 6:15.

I wake up to find myself alone in the bed. I can hear the shower running. I get up and join them in the shower. Brad manages to cum in each of us.

Breakfast is room service. I open the door to the waiter. He blushed a bit and scans my nude body. As soon as he is in, Serena gets up to see what he has brought. I find my plate, and Serena finds hers. I take the last plate to Brad. Serena asks the waiter for the bill. I watch her rub his cock while reading the tab. Then she brings it over and Brad signs it. Serena takes it back to him, takes his hand and puts it on her breast, then kisses him.

When she breaks, he says to Serena, "Thanks for the tip." He rolls his cart out and the door closes.

Serena looks at us. "I like to tip the waiters with something they don't usually get. They remember me, and that gets me really good service next time."

We eat breakfast, then Brad suggests we take a walk. "There is a nice park not far from here. Then we can walk up Marely Road and do a bit of shopping. I need to get something for my mother. She is not easy to buy for."

I get dressed, and excuse myself to go down to my room and get fresh clothes. Serina has several outfits in her bag. We agree to meet in the lobby in 10 minutes.

I quickly change and shove the cash into the hotel safe. I get down to the lobby slightly before they do.

I notice that Serina is wearing heels. Not ideal for walking. "Brad, I see Serina has heels on, maybe we should start with a shoe store so she can pick up shoes more suitable for walking."

He looks down at her feet. "I had not thought about that, sure there is one not too far from here."

We get her some cheap running shoes that are much more suitable for walking.

The next couple of hours we spend trying to find something for Brad's mother. It is not helped by her increasing dementia. Eventually he finds a little glass bird and decides that it will work. She had several when she was young, and it might trigger some memories. By this time lunch is becoming an issue so we find a little restaurant and eat.

After lunch Brad suggests we visit an Art Galary not far from us. Weird, I had never seen Brad as 'cultured' and I never bothered to visit one in the past. The gallery had a modern art show, as well as some of their own catalog, mostly European masters. The modern art was pretty much incomprehensible to me. I cannot see the point of a canvas where someone has thrown paint at it. Even kindergarten children can manage to draw a basic scene.

The European masters were much better, at least you could understand what was going on. There was a statue of a nude woman, probably 5 feet tall. It was exquisite, smooth lines, and you could see an expression of joy on her face. I had never seen anything like it and resolved to spend more time looking for sculptures.

After the Art Gallery Donna suggests a walk-in a nearby park, followed by dinner at a restaurant she knew. I must remember to think of her as Serena or I could blow her cover. Finally, we end up back in Brad's bed for the night. Not a lot of sleeping going on.

After breakfast, Donna gave me her contact information and I went back to my room to get some sleep before work on Monday.

About a month after we got home from the trip, I had a call to Brad's office.

"Close the door."

I closed the door and took the chair opposite his desk.

"Your friend Angel. Do you think she would like a week at an all-inclusive south of Cancun?"

"I will check, but I suspect she would be available."

"Good. Any chance her friend Serina would like to join us?"

I smiled. "I can check. I know she does not normally take travel jobs, just too much opportunity for things to go wrong, but in this case, she might be persuaded."

"Please check. I am thinking the week of the 15th next month. She has not posted a weekly rate on her site, so find out for me."

"OK, anything else?"

"No, though maybe you should book off a couple of days before we travel so it does not look quite like we are away together."

"Sure, and maybe a few days after as well." I got up. "Do you want the door closed?"

"Nope, just for this conversation."

On the way down the hall to my office I started to think about what I would do with the extra income.