20 questions

I am a happily married travelling salesman who spends about 70% of the time on the road all over North America. This is a true story of what happened on a recent selling trip. Please forgive the length as it will probably have to come in several parts.

It gets very lonely on the road but I try to stay in touch with my wife of almost 15 years with calls every second or third night. Some of these calls become very steamy following which, or during, we will each masturbate to relieve some of the tension. Just hearing my sexy, lovely wife panting and getting off on those times when we ‘do it’ while on the phone together is enough to send me over the edge as I imagine her fingering her wet pussy and convulsing in climax. Unfortunately, while it takes the sexual edge off it doesn’t relieve the loneliness of being close to someone. This might explain what happened recently.

The time when I feel most alone is when I am in a restaurant by myself for dinner. About half the time, I would dine with a prospect or a client; but there are still many times when I will be in an unfamiliar restaurant eating silently watching couples, families or friends eating and happily engaged in conversation. That was the prospect this particular Thursday evening when I was directed to a small table for two in a corner of the hotel restaurant.

As I looked over the menu an attractive brunette, wearing business attire, was seated at the adjacent table. We exchanged a brief, but distant, smile as she took her seat and the server removed the extra place setting from her table. She was obviously a road warrior like me. I then did something completely out of character.

“Excuse me”, I said, “You look like a fellow business traveler. I have been on the road for about two weeks now. How about you?”

“Too long” came her reply not looking up and still studying the menu options. While not an overly friendly response I was eager to speak with someone about anything other than my company’s products, so I pressed my luck.

“I know how that is. A different city each day, a full agenda and yet at night I find the hardest part dining alone while everyone else in the place seems to be having a good time. My name is Paul” I said as I extended my hand.

“Rachel”

“Rachel, would you care to join me for dinner? I’m happily married and perfectly safe. I would just like to enjoy a meal talking about anything but business”

Rachel studied me for a few seconds and then moved to my table saying “Why not? That would be nice.”

Over appetizers and more than a half bottle of wine I learned that she was five years younger than me (in her late 30s), married with two children and lived on the East Coast. I learned her likes and dislikes about her job, the grind of the road, where she went to school, etc.

I had asked her what was the most interesting thing she had ever done, the scariest, memorable, funny and embarrassing by the time we were into the main course and a second bottle of wine. It was then that the questions changed tone and became far more interesting. I asked her what was the sexiest thing she had done?

She stopped eating, looked at me and then a smile came to the corners of her mouth as she leant across the table, closer to me.

“I once stripped at a club that had amateur hour,” she whispered. “I went there with a bunch of girlfriends for a few drinks and the announcer asked for volunteers from the audience. After a couple of girls tried dancing and one of them chickened out, I said I could dance better than that, so my girlfriends dared me to go on stage and the rest is history. It was very sexy taking off all my clothes in front of friends and strangers. So what’s the sexiest thing you’ve ever done?”

“I once was at this strip club when this sexy brunette got up on stage….,” I teased. Then she laughed.

“So what’s the most sensuous thing you’ve ever done?” I probed.

“Ohh no, you ducked the last question so you go first,” she said sipping another glass of wine.

“That is easy”, I quickly replied because I really wanted to hear her story, “I once took a massage course. Everything about massage is sensuous, from the smell of the oil to the warmth of the skin. Ideally there is also soft music. I’ve given my wife, her sisters and several of her girlfriends massages. I must be doing something right because they keep coming back for more.” I wanted to keep it light but keep the conversation moving forward. We were flirting, harmlessly, and we both knew it. “Your turn!”

“Sex on the beach and I’m not talking about the drink. That was a long time ago, before I met my husband actually. Have you heard of Little Beach on Maui?” Not waiting for an answer she continued, “We were on vacation and my boyfriend said we were going to the beach. I didn’t know it was a nude beach until we got there, laid out blankets in a more secluded part of the beach and he started taking off his clothes. Little Beach is just off Big Beach, where everyone wears clothes, so I didn’t notice that the few people on Little Beach were naked.”

“The sun was warm on my skin while the breeze took the direct heat off. My motor was started by putting sunscreen on parts that hadn’t had sunscreen before. I was laying on my stomach as my boyfriend put some sunscreen on my butt cheeks but he also took the opportunity to slide his fingers lower and toy with me. We ultimately ended up spooning with him behind me. It was so good but very frustrating.”

“Why?”

“Because we had to move slowly so others didn’t know what we were doing. They don’t call it Little Beach for nothing. While nudity is tolerated, I don’t know about full on sex. It was very sensuous though with the sounds of the surf, the heat, the slow rocking, the continued tension and fear we would be found out.”

“You definitely beat me on that one” I said pouring the last of the second bottle of wine into her glass. I sensed she was really enjoying our game, so I pressed on. “OK, let’s see. What is the most erotic thing you’ve done? The thing that turns you on the most.”

“You mean I can only pick one?” she said with a slight wink just before sipping her glass. At that point I didn’t know if I had gone too far and she would bolt, defer on the question, or…… “I don’t know if I’ve come across my most erotic (she half whispered and mouthed the word ‘erotic’ recognizing we were in a restaurant where someone may overhear us ) moment. You know they say it is only kinky until you try it. I think it might be the same for this too. Let me think about it while you tell me yours.”

She had turned the tables again and now I was on the spot going first. I realized that she might gauge my response to tell me something that was on the same level. If I went too far over the top for her, that might end the conversation and she’d think I was creepy. But if I told her something more tame, she might think I was a prude. It was weird because I had just met her and after dinner we would go separate ways because I wasn’t going to sleep with her (I never cheat on my wife). Yet, here I was caring about the impression I was about to make. Once I had that split second insight I decided I would just lay it out on the table and what would happen, happens.

“The thing I find most erotic is either watching or making a woman cum”. I studied her face to see if I hit a nerve with such a direct word. She really had a poker face, but she again leant forward. “Let me explain with a couple of examples,” I continued. “Let me tell you about the time I gave, Susan, one of my sister-in-laws a massage.”

“She had driven across country to visit us with one of her friends. It took her two days and when she arrived Susan complained to my wife, Lisa, that all the muscles in her neck and back were sore from the long hours at the wheel and a bad motel bed the night before. My wife suggested that I give Susan a massage, while my wife chatted with Susan’s friend.”

I continued, “I laid out a towel on the bed while Lisa led Susan into the en-suite with a towel to cover herself and instructions to strip down. When Susan came out I told her to lay on her back so I could start with her neck before moving on to give her a scalp and facial massage. I undid and draped the towel she was wearing over her body so she was covered from her armpits to half way down her thighs, and started the massage.” Rachel continued to sip her wine.

“I then had her roll onto her stomach so I could massage her back and the back of her legs. I held the towel so Susan could roll away from me and still be covered. I had her slide her hands under her hips so she would be more comfortable. I massaged her from the shoulders down her back, over her butt and down the backs of her legs.”

“It was time for Susan to roll over for the last time but before I could grab the towel, she rolled onto her back cupping her hands between her legs to cover herself. She told me she was too warm under the towel and although she was now topless and almost fully nude, neither of us minded,” I said. That slight smile at the corner of Rachel’s lips returned at this part. She seemed VERY interested in what I was saying.

“I started to massage Susan’s feet when I thought I noticed her hand moving ever so slightly under the cover of the other hand. As I moved up her legs the movement was obvious and blatant. She was playing with herself. She no longer was hiding the fact that she was masturbating as my hands moved up just past her knees. As I massaged higher on her leg her movements became more frantic and her breathing more labored. When she came it was a very erotic and intense moment for both of us.”

Rachel just continued smiling while holding her wine glass in two hands. The waiter came up and cleared the plates and offered the bill.

Rachel reminded me I said two examples. I offered the less risqué of the two first to judge her reaction.

“Right, the other one happened just three months ago. My last prospect of the trip blew off my appointment, due to illness, so I was able to catch a much earlier flight home. After being on the road for almost three weeks I was eager to see Lisa,” I explained.

“As I drove up that afternoon I saw Lisa’s friend’s car in the driveway and found both Lisa and Kim by our pool, tanning topless. And yes Rachel, just about everyone in Southern California has a pool”, I added chuckling. Lisa told me a long time ago that because our backyard is very private and I’m away a lot, several of her girlfriends feel comfortable enough to stop by to tan topless and I suspect a few tan in the nude too.

“I noticed that one empty wine bottle was beside the ice bucket and the girls were just emptying the second into their glasses as I walked out. Lisa was pleased and excited as she jumped up to meet me. It was obvious she was a little tipsy and Kim probably was too. After a sloppy wet kiss, Lisa suggested that I change, poor a drink and join them.” I left out the part where Lisa hunched her pubic bone against my upper thigh while she kissed and hugged me to let me know I had a bigger welcome coming later.

Rachel interjected. “I suppose now you’re going to tell me you had a threesome. That is such a cliché that I think you’re making this up.”

“Nope,” I countered smugly knowing the truth. “Wrong on both counts. I never took off my clothes.”

“Then it was girl sex?” Rachel looked both very interested in that possible story line and a little perplexed.

“Sorry wrong again,” I said just as the bill was brought to the table. As I signed both dinners to my room I sat in silence as Rachel must have been thinking what I was about to tell her. While she almost seemed upset at the possibility of being strung along a minute ago, she now was definitely intrigued. Rachel touched the top of my hand as I slid the signed bill to the waiter.

“Sorry, I didn’t mean to interrupt.”

“As I got to the patio door on my way to the pool I heard the girls laughing,” I continued. “Kim asked Lisa if she ever had a G-Spot orgasm? I think the girl talk that afternoon had been about sex. Lisa said she had many a time and asked Kim if she had. By this time I had sat at the end of the chaise lounge Lisa was reclining on. Lisa looked up at me and told me that Kim “the poor thing” hadn’t had one of those really intense orgasms.

Kim then asked Lisa what it felt like and was it really good? My wife spent a few minutes trying as best she could to describe the feeling. And yes, Lisa said, they were really, really good.

Kim half laughed and said she needed to learn how to do that.”

“I thought everyone knew how,” Rachel blurted out then covered her mouth and looked around the restaurant to see if anyone heard her. “I mean, doesn’t everyone read Cosmo at least once?”

“I guess not,” I said shrugging my shoulders. “Anyway, my little minx slid off her bikini bottom as she said “We’ll show you!” and placed her legs on either side of me.”

Rachel’s mouth dropped open. “You’re making this up.”

“No I’m not,” I told her truthfully. “Don’t forget I was away for almost three weeks, the conversation was somewhat graphic and my wife was feeling no pain from the two bottles of wine. But to cut to the chase, I’m no fool so I started to stroke her and then massage her G-Spot while Lisa was describing what I was doing inside her. Her talking didn’t last very long before she got lost in what we were doing and then she climaxed, in front of her friend.”

While I didn’t tell Rachel this, Lisa’s friend Kim was practically falling off her lounger to get a better look at what I was doing. I also didn’t tell her that Lisa gets very wet during sex, so the sounds of my fingers inside her pussy combined with Lisa’s moaning and orgasm must have turned Kim on as much as they did me.

“After Lisa came, all Kim could say was ‘WOW.’”

“That must have been quite the show,” Rachel half whispered.

“I certainly thought so,” I said smiling. “But the most unexpected thing happened next. Lisa turned to Kim and said ‘Your turn’. Although Kim hesitated at first, Lisa pointed out that I knew what I was doing so the chances were she would have a good first experience and Lisa was sitting right next to her. Before I knew it I was doing the same for Kim as I just did for Lisa. Now, Rachel, I must be honest and say I don’t know if I’m that good or if it was the whole setting or if Kim always has strong climaxes but it was incredible, beautiful and highly erotic. What I also thought was sexy was that Kim reached out for Lisa’s hand just before she came and they held hands through it all.”

“And so what happened next?”

“Nothing. Well, later Lisa and I had a great time; but at that moment, nothing. Lisa asked that I bring them both some water and I refilled my drink. I guess Kim felt a little uncomfortable being married and letting me bring her off. But Lisa again pointed out that I was fully clothed, she was there, nothing more was going to happen between Kim and I, and it really wasn’t much different that using a toy to masturbate. As my wife said, all Kim did was substitute my fingers for the toy. Plus,” I added, “Kim had just learned something new she could bring to their bedroom. After thinking about it Kim agreed and felt better. And the rest of the afternoon just carried on, as always.”

It seemed as though the server always timed his approach to the table when we could have just finished talking about the weather because he seemed none the wiser to our real conversation as he asked us if we wanted anything else even though we had closed our tab.

We took that as a cue to leave. We went to the hotel elevator and selected our respective floor buttons. On the ride up I thanked Rachel for the great conversation and apologized if it had become too intimate. I told her that sometimes it is easy to open up to strangers in a very personal way even though, or particularly because, it is only for a few hours never to be repeated.

As Rachel’s was the first floor the elevator stopped at she said she had a great time, was thankful she accepted my invitation to join me for dinner, even though she rarely drinks that much, and said I lived an interesting life. When the elevator door opened Rachel said good night with a light peck on the cheek and stepped into the hallway.

Just as the elevator door was closing, I held it open. “Wait, Rachel. I just remembered, you didn’t tell me your story.”

She smiled, crooked her finger and did the ‘come here’ waggle. And that is another story.

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