Friends Give Me Erotic Challenges

This is the fifth chapter in this saga. It can stand alone but is probably best if the first four chapters are read prior to this. As always, there are the disclaimers: no real person or name is represented and please do not copy or distribute this material without permission from the author.

So, please read on and hopefully enjoy.

= = = = =

Megan and Susan were at their usual table when I joined them for lunch the following Saturday. I looked at them wondering if anyone other than me knew their secret. Two well-dressed, sophisticated, women, both looking like what they were, professionals. Megan and Susan were both lawyers but practiced in very different areas of the law.

What would anyone think if they had the same visual image of them that I had. Susan sucking on my husband's cock and swallowing his cum. Megan eating my ass and sucking a massive load of sperm from me. No. There was no way in hell that anyone could guess what these ladies did in their private time.

After that tryst with their two husbands, both ladies had their own fun by exploring me with their mouths. Every inch of me had the pleasure of two female tongues, mouth, lips, and even teeth. This was my first lesbian tryst since college, and they were wonderful. They ended the event with Susan sitting on my face and riding me to her orgasm while I nearly drowned in her juices. At the same time, that beautiful redhead Megan had her face deeply buried in my crotch and she sucked on me and drank my fluids until I also reached a delightful orgasm.

So, now, when coming to that table for lunch I had those incredible memories and images of my two friends as well. Holy hell but things had changed since we started all of this just a few weeks before.

"So, how was Des Moines?" Susan asked, knowing that I had just returned from yet another business trip the day before.

I had gone there for a short one-night trip where we met with clients and various presentations on our new products were given, including one from me. Among the people in the small audience was my boss, Frank. That same man whom I had been naked for in that private strip club booth. I had given him my first lap dance ever and he had brought me to climax as I rubbed my bare crotch against his pants-covered cock.

He was there in Des Moines with me and had all been in true professional mode. Throughout the whole trip, he acted simply as my boss and colleague. Nothing more. During one marginally private moment with him at the hotel bar I had tried to bring the topic up. His response was simply to give me a charming smile and say this wasn't the right time or place. So, oddly, that whole incredible topic was set aside.

Now, I was having lunch with my two best friends, and everything was being treated as if this was a normal day, a normal lunch, and a normal chat between three mature women.

A younger man, probably in his late thirties, strolled by the table and I could see him try to get a second look at me and my two companions. This was flattering.

"You'll find that after doing the kind of things we've been doing you'll get more second looks from men," Susan said in acknowledgment of the man's glances. "It is as if these activities build some sort of sensual glow."

"Or a 'come fuck me' look," Megan laughed. "Janet, you now have a new sexual energy about you, and men can tell. They just sort of know that you aren't a prude, and you will, in fact, happily spread your legs."

I could only agree. My friends gave off a healthy and sexy look and I was happy to know that I was doing the same.

"Are you ready to build on that glow, so to speak?" Susan asked.

"I was afraid you'd never ask. So, what new experience do you have for me?" This was the part of my chat with Susan and Megan that I was really looking forward to. It was also something that my husband and I had talked over several times lately.

Both Jack and I were excited and wanted our activities to grow. After his watching Mark and Sam fuck me in so many ways, and then watching me with Susan and Megan later, he was now perpetually turned on. Put another way, we were screwing like newlyweds. Put yet another way, I was surprised I could walk, I had been screwed so many times by him lately.

For me, the excitement was in gaining new sexual experiences. My husband's excitement was in watching me have those experiences. And, in the worst case, if he couldn't watch me in action, he would get excited just from hearing about them.

Me a newly developed exhibitionist and blossoming pervert and my husband, a voyeur and wannabe cuckold. What a pair.

"So, Janet," Susan began her explanation. "First, I need to tell you that the room where you had your tryst with our husbands and, well, with us, last weekend, is actually the playroom for a small club. A sex club if you will."

"Like a wife-swapping club?"

"Nah, that my friend, is way too simple," Susan said. "No, there is a small group of eleven people who get together once every other month down in that room. It all started with just Megan, Mark, Sam, and me getting together. Well, another person who will remain nameless for now, found out about us and kind of took over. That person is now the group's leader and he or she has approval over all potential members. The group leader can also be perverse as hell!"

"Because of our leader," Megan joined in, "we have experiences that we never would have dreamed of before. It keeps things fresh, fun, and exciting."

"What kinds of things do you do?" My curiosity was really up now.

"You can't know until you're a member. I can say that for each session there is a different theme, and the group members take turns deciding what that theme will be. They range from simple fucking to some pretty crazy things."

"I know that I don't even have to ask my husband. Jack and I want to join!"

Megan chuckled. "Not so fast. Not so fast. There is a set of initiation rites which you must do first."

"Janet," Susan took over the explanation. "Think of this like a college fraternity initiation. What happens during those initiations can be pretty extreme. Then, in those fraternities, once the person completes the initiation rites, activities from there are much tamer. That is how this will play out."

"Sounds fun," I answered, not having a clue as to what the 'fun' might entail.

"Okay, well you asked for it," Susan said as she took a long sip from her coffee. "There are five tasks which must be completed. Two of them are specific to your husband. The other three are specific to you. I warn you, the last two are really twisted."

"What are they? What do we have to do?"

"Nope, all we'll do at this point is to set up the first initiation rite. Are you and Jack free for tonight and, maybe even into tomorrow?"

"Yes. We have nothing on our schedules. Nothing until Monday morning when we go back to work."

"Okay, please leave the table for a few minutes. We need to make some calls to set things up."

I got up and went across the room to stand near the entrance to the women's room. It took almost twenty minutes but finally, Susan motioned for me to return.

"Everything is set," Susan said. "Both you and Jack are to go to the restaurant in the Hilton downtown at seven PM this evening. You should each dress to impress. He will be on a date with a member of our group. You will also be meeting someone, and that person is not a member of the group."

"So, we'll be on some sort of date with other people and who are these people?"

Megan laughed. "Oh, you will know them when you see them. And, no, you aren't both on dates. Jack is and should do his best to impress his date. You will be on, well, an assignment. Jack's date, by the way, will be acting as your pimp."

"I have a pimp now?" What the hell had I gotten into?

"For tonight, and only tonight, yes."

"One last thing, Janet. Both of you and Jack need to do everything you can to succeed in this first initiation rite. If either of you fails, then you are permanently out of the running to join our group. There will be no second chances."

Holy crap. Again, what am I getting my husband and me into? I should have been put off by all of this and said hell no. Instead, I was completely looking forward to it.

= = = = =

I recognized them immediately when the restaurant hostess guided us to the table where they were sitting and waiting for us. I could not have been more shocked!

My boss Frank and Susan and Sam's daughter Sally were waiting for us! What the hell was going on?

"This is a joke, right? Are we on some sort of candid reality TV show or something?" I exclaimed as Frank stood, pulled out a chair for me, and guided me to sit down.

Sally, a delightful young woman with long blonde hair, laughed playfully. "No joke. Really. No TV cameras either although that is a great idea."

Jack and I have known Sally since she was in grade school. Hell, she and my son had dated in high school. Now, at the age of twenty-one, she was a strikingly beautiful blonde. I know that my husband thought she had grown into a beauty as he had said so more than once.

And Frank was here. How was it that my boss was here? I asked Sally and she said that when Frank had come out from that private booth in the strip club, her mother, Susan, had an idea. She had remembered that I knew him, and she could also see that Frank was a classy and refined-looking gentleman. So, she approached him and got his contact info, just in case it might come in handy someday.

That "handy day" had arrived. Frank explained that when Susan had called him earlier in the day and told him her plans, he readily agreed.

After hearing all of this, several thoughts, especially about Sally, were racing through my head. But, first, I had to clear things up with my boss. "Frank, uh, this is embarrassing, to say the least. Do you know why you were asked to be here and what might happen?"

"Uh, yep." He gave me one of his charming smiles which tended to melt me. He had been briefed on what might happen and he had agreed. A big part of that agreement, I later learned, was that he knew if he didn't say yes, some other man, some stranger, would be chosen and that was bothersome to him in many ways.

"And you want to do this. Whatever the 'this' is?"

He just nodded his agreement. So, I turned my thoughts and attention to that beautiful young blonde. "Sally, uh, from what your mother told me, you're something of a leader of their club?"

"I am not 'something of a leader' I am the leader. That playroom down in their basement is there because I made them do it. My club. My rules. Their basement. Period."

"Okay and uh wow," I exclaimed. "Uh, Sally, this is awkward to ask, but does this mean that you have sex with your parents?"

"Oh yeah," She gave me an odd smile. "If we let you join, you will find other interesting relationships among our little group as well. Now just order your meals, please and we can chat more about this later."

So, meals and drinks were ordered and soon our focus was on what was on our plates. Finally, Sally spoke up again. "Tonight, right after we dine, we are going to split off. You and Frank will go off to one room upstairs we have reserved, and Jack and I will go to a suite. We get the better room and what we do up there will be just between us."

"We don't keep secrets, Sally," I explained while also trying to process the concept of my forty-five-year-old husband taking this beautiful twenty-one-year-old to a hotel room for sex.

"Uh, okay. The meal is over. Get out of here and take your 'we don't keep secrets husband' with you."

I was shocked at this abrupt and harsh tone of hers. What the hell was going on? I looked frantically around the table. Clearly, Sally was the only one who was fully in the know here.

"Janet," Sally said, which was interesting because she had never addressed me by my first name before, "A fun twist to this adventure is that sometimes you will in fact keep secrets from each other. You won't be allowed to tell Jack anything about what you do with Frank, and he isn't allowed to tell you about what he and I do together."

"That is kind of risky to a relationship, Sally," I said, putting myself in parent mode.

"Yep, and I like it that way. Some people would say that not telling your spouse about the sex you are having with someone else is just plain stupid. For me, playing with the mind is part of the fun. This thing we do isn't just about your body. Now, listen to me, everyone in our group has done this. Mark, for instance, has no clue what Megan does when she is on one of these dates and so it goes. And, lady, this has only strengthened the relationship of every couple in the group. You can ask them later."

I looked at my husband and gave him a questioning glance. He nodded his approval. Well, hell, of course, he would approve given this opportunity to have sex with that luscious young woman. "Please, Janet. I'm okay with this." He was almost pleading.

It would seem that my husband was about to screw Sally and I would not be allowed to know any of the details. Holy fuck. Again, what have I gotten us into? So, I needed to look at the flip side of this whole crazy thing. I might just be having sex with Frank, a handsome, trim, and sophisticated man who I had something of a crush on ever since that strip club event.

My response, after several minutes of mentally processing it all, was to look at Sally and say I would agree with the terms.

"One more objection and you are out. Got it!"

Wow. I was still stunned by this crazy turn of events.

= = = =

"Frank," Sally said several minutes later as we sat there at that table in the center of the restaurant. "You know that these two have to pass several initiation rites before they can join the club I created. You also were told that for Janet to pass this first test she must have sex with you."

"Yes, and I am still dumbfounded about all of this. And, Janet, are you okay with this?" He looked at me.

"I am looking forward to it Frank," I said honestly.

Sally then took back control of the conversation. "You two... it is not as simple as just going off to a hotel room to fuck." She turned her attention to Frank. "Here's the deal, she must be a cheap whore for you tonight. Not a lover."

I sort of saw this coming but still was surprised to see what happened next.

"Here is her rate card, Frank. I'm her lady pimp for the night so you have to pay me if you want to use this slut sitting here."

So, we were back to calling me a slut and now a whore. And again, I wasn't objecting. What did Frank think about this or about me right now?

Frank took the card which was handed to him causing him to laugh. "Uh, these rates are surprising, to say the least."

"I know, for an inexperienced whore like her those rates are probably high, but well pay it or forget about it." Sally was clearly having fun with this.

My husband stayed silent. Any normal husband in a normal situation would get pissed. But this wasn't a normal situation and both Jack and I were enjoying this weird and perverse situation. I was glad that he wasn't trying to be difficult about Sally setting me up to be a prostitute for Frank.

"So, Frank, what are my rates?" I nodded to the card he was holding.

He laughed softly. "Ten dollars for one hour with you and you must give me a blow job. Or, if I want to pay twenty bucks, I can have ninety minutes and fuck either your pussy or your face but not both. The biggest rate is forty dollars, and I can have you for the whole night and can fuck any hole I want as many times as I want."

I laughed out loud. When Sally was calling me a cheap whore, she wasn't kidding. "That's all I'm worth?" I looked over to Sally.

"Yep," she laughed then turned back to Frank. "So big fella, what is it going to be?"

"Oh, definitely the forty-dollar package where I get her for the whole night." Frank was doing a great job of playing along with this odd game.

With this negotiation complete and Frank paying Sally I realized that I was now officially a cheap whore. There was also one huge aspect of the evening that was unclear to me. "Sally, since I will be a whore tonight to fulfill this twisted initiation rite, what does Jack do?"

"He has to bring me to orgasm at least once. So, Whore, his job is much harder than yours. You are simply a set of holes to fuck. He is the one who is really facing the pressure to perform."

Fascinating. Abso fucking lootely fascinating.

With this done, and our dinners completed, Frank led me away from the table, while we left my husband with that luscious young blonde back at the table.

= = = =

I half expected Frank to ravish me once we entered the hotel room. Given the whole 'cheap whore' thing, and the fact that he had paid just $40 for the use of my body, it would have been reasonable for him to have me on my back or knees to service him.

Instead, Frank was, well, Frank. A pure gentleman. In some ways, it was almost as if he thought that by his being my 'client' that he thought he was saving me from other possible clients. I didn't want to be saved. But I followed his lead and sat on the small couch in that room while he ordered a bottle of wine from room service. That wine, by the way, cost more than he had paid for the use of my body.

As we sat and sipped our wine, he surprised me with the admission that he had a strong attraction to me. He even admitted that if I was single and he was younger he would have pursued me as a romantic partner.

"Damn it, Frank," I responded in a soft voice. "I have feelings for you too and, well, we can't be lovers. We can only be sex partners." Saying this, I stood from that little couch, stepped back, and slowly removed that little black dress I was wearing.

Once the dress was off, I stood before him wearing only my sexiest, tiniest set of black bra and panties and heels. I knew that I looked damned good right then.

"You are luscious, Janet. Your husband is a lucky man."

"No, Frank. You can be the lucky man. My husband is getting lucky with Sally right about now and it's time for us to do the same."

"Why are you doing this? It was wild enough to encounter you in that strip club, but whoring yourself to me? I don't get it."

I had been thinking about this very thing myself. "I think, Frank, that it is because I have been looking for some excitement. Ever since I started accepting these erotic challenges and adventures from my friends, I have felt more alive than ever. I have a wonderful career with you and a loving husband which I adore but the word 'excitement' isn't part of that. I think both Jack and I needed something like this.

Or maybe I could have taken up skydiving, climbing Mount Everest, or something."

It was time for talk to stop and it didn't seem like Frank was going to make the first move. I stepped over to where he was sitting before me and guided that handsome, silver-haired gentleman to his feet. Then I leaned into him and soon we were in a passionate kiss.

Screw my earlier statement that we couldn't be lovers. That kiss was a delicious mix of love, desire, and passion. Still, he was only kissing me. Even with that lap dance we had done in the strip club a while back; he wasn't making a move on me. I could feel his cock pressing against me through the clothes, but that was it.

What would a paid whore do with a reluctant client such as Frank right now? I had no actual knowledge of this but did what I thought a good whore would do. I undressed Frank. Slowly and as seductively as I could I removed his suit coat, then his shirt and T-shirt. Then I gently kissed and nibbled on his nipples which were in the center of a delightful forest of silver chest hair.

I guided him to sit on the edge of the bed and then removed his shoes and socks while gently rubbing his feet and ankles. All the while, he was looking down on me with desire.