Giving More Than Advice

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Sister-in-law needs a help with more than her business.
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4.51
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Part 1 of the 2 part series

Updated 10/15/2022
Created 12/14/2008
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Robeth123
Robeth123
36 Followers

(This story may be true, but the names have been changed)

Friday afternoon:

Finally, some time alone. It was the day after Thanksgiving and I was waving goodbye to my lovely wife of eighteen years and our four children as they were leaving to visit her parents for the remainder of the holiday weekend. I was scheduled to go with them but after an unexpected meeting came up for Saturday morning at the university, I had to stay home. I was trying to act sad but the truth is that I love my time alone. Time to read, reflect on plans for the coming year, and who knows what else. Maybe I would get a chance to spend some time with Allison, who I have been growing quite fond of lately. Of course it wasn't always that way.

It all started twenty-two years ago when I first met my wife's sister Allison at a party on campus. Beth and I weren't even officially dating yet when she introduced me to her 18 year old sister, who was in town to check out the university. Allison had a darker complexion than Beth and was taller. She was not extremely curvy but she had this Liv Tyler movie star look with long black hair and beautiful brown eyes. It didn't take long to discover that Allison knew she was gorgeous, which made her extremely stuck up and I doubted anyone would ever penetrate the "I am better than you" shell she had built around herself. Her attitude toward me was that I was not good enough for her sister, and that made us instant adversaries that would carry on for a long time.

A couple of years later, Beth and I were married and we settled in the college town where we had graduated. Allison went to an Ivy League school and we only saw her around the holidays. Being very driven as well as beautiful, Allison became very successful as a writer, a motivational speaker, and has recently started a successful business. A few years ago she married John, a man seven years older than her, and they had a couple of kids. To me it seemed to be a marriage of convenience and it was hard to tell if they were truly happy.

Around a year ago, Allison and John moved about twenty miles from us because they wanted to raise their kids away from the big city. Seeing so much more of them I realized that although Allison was still strikingly gorgeous, she had mellowed a lot and was actually pleasant to be around. Since I had my MBA, she was asking more questions as they related to her business and I always jumped at the chance to help. Not that I had ulterior motives, I just knew it made Beth happy to see me help out her little sister.

Although Beth and I were extremely happy, I found myself having more in common with Allison then I first realized. When we would all travel on ski vacations, Allison and I would hit the expert slopes while everyone else would ski the easy stuff. When we would all go to the beach, Allison and I would go for a jog while everyone else sat around eating and drinking. It wasn't that Allison and I liked each other (we still acted like adversaries); it was just convenient for us to hang out together. However, even though she's my adversarial sister in law, she still looks awesome in her jogging outfit and with the ass she has, I found myself falling behind quite often when we would go for a run.

That brings us to last Thanksgiving weekend. Being in our forties with kids, Beth and I find ourselves staying at home for the holidays more instead of traveling hours away to either side of the family. Imagine my glee to discover that not only did we not have to travel but we didn't have to cook either, as Allison and John had decided to have us over for Thanksgiving at their house. Even though Allison had mellowed out, she still had a selfish side about her and I quickly discovered what it was. She was using this dinner as another opportunity to pick my brain about a new compensation plan she wanted my help with for her business, which she asked about from the moment we arrived until we left.

During dinner, John shared that he was going to take their kids up to his parents and spend the rest of the weekend with them, but that Allison was going to stay home to wrap up some end of the month business responsibilities. Beth shared that she was doing the same thing but that I couldn't go because of a prior engagement, and Allison instantly locked eyes with me. I said, "I know what you're thinking, but you have to finish your compensation plan without me." She smiled a wicked grin and Beth encouraged her to call me at any time if she needed help. Beth reiterated, "Robert has a wonderful business mind and if I were you I would glean as much of his knowledge and experience as you can." Then she openly encouraged me to be available at Allison's beck and call. She did so by saying, "Bobbie, if you give Allison your best while I am gone, I will give you my best when I return". We all laughed at her playful appeal with a sexual innuendo, as it was a little out of character for her. At the time I tried to act put out by the idea, but I secretly hoped she would need my help.

Saturday afternoon:

By 4:00 in the afternoon, I feared that Allison had worked out the details of her compensation plan on her own and my help was not needed. That's when the phone rang....

"This is Robert," I answered

"Robert, its Allison."

"Hey Allison, enjoying your time alone?"

"Yeah, except I can't get this stupid spreadsheet to model the compensation plan properly."

"That is too bad," I said, not offering any help. She paused for a moment and countered, "Now Bobbie, remember what Beth said about being available to help me out." I nearly chocked. She had never called me Bobbie before. No one ever called me Bobbie except Beth. I was Robert to the rest of the world and Bobbie was the pet name Beth used for me; especially when she was feeling playful. I knew Allison was using it only to bring to mind the conversation from two days ago but still hearing her say it and the way she said it made my mouth dry. However, I still played a little hard to get.

"Yeah, she said I would be rewarded if I helped, not obligated to do so." Another pause.

"Ok, how about this," Allison countered. "You have to eat sometime tonight. I will make you dinner and you fix this damn spread sheet. And on top of that, you get rewarded by my sister so you can't lose. Do we have a deal?"

Still not wanting this line of discussion to end I said, "Well, your sister is the one that really has nothing to lose because she loves our little reward time as much or more than me".

Allison laughed, saying, "I doubt any guy has less fun than a woman in a situation like that unless he can't get it up."

I came back with, "That's not the issue at all, but to keep this on a professional basis, I won't go into that. I'll be there at 6:00." She simply said "See you then". I could tell that she was a little frustrated because she is the one that normally ends the discussions and sets the rules. But now, the tables had turned.

I couldn't wait for 6:00 to arrive. I showered, put on some trendy jeans and one of Beth's favorite shirts that I wear when we go out. I didn't want to look like I had anything in mind, but at the same time I was secretly hoping something might happen between us. When I arrived I found Allison on the back deck having a glass of wine and a cigarette. This was a little out of character as no one in our family drank much and normally it was for social reasons. The other notable fact was that instead of being decked out like I was, she was donning sweat pants, a tee shirt, and had her hair pulled back with no makeup on. Still, she looked drop dead gorgeous.

"What are you all dressed up for?" she asked. I played it off like I was still dressed from the meeting earlier in the day. When I asked about the wine she said, "With the family gone I thought I would have a little unwind time.." When I asked about the smoking she said, "I normally smoke about one pack a year and normally alone. It's an ugly habit but it goes so good with this deck wine I am having."

"Mind if I join you?" I asked.

"I didn't know you liked wine?"

"There are a lot of things you may not know about me."

"What makes you say that?"

"Well, you didn't know I liked wine."

"Touché, but what else don't I know?"

"Look, pour me some wine and let me get your plan put into your spread sheet correctly so we can eat." She reluctantly succumbed to my request. Once again, I was in charge and she did not like it.

About thirty minutes later, she came into her office to see me putting the finishing touches on a beautifully constructed compensation plan. She seemed overly excited and said, "Robert, when did you get so smart?"

Knowing she was still sipping wine while she cooked and feeling a bit more bold from the wine myself I said, "I've always been smart. You were just too self focused to notice." Her mood turned on a dime and I thought I may have said too much. She then shamefully looked down and then into my eyes and said, "I have really been a bitch to you for the last twenty years."

I tried to lighten things up by saying, "Not really, just for about nineteen. Last year has been almost bearable." We both laughed and she instructed me that I had fulfilled my end of the bargain and dinner was waiting.

The next hour represented one of the best discussions Allison and I had ever had. She had prepared a chicken pasta meal which went great with the second bottle of wine she'd uncorked. Over dinner we talked about business, family, and filled in some of the gaps from the last twenty years.. When I spoke about how much I loved her sister, she started to cry. When I inquired as to why, she waved me off for a moment. She then admitted that her marriage to John was really more for convenience than love and that it left a little to be desired. I encouraged her by saying that my marriage to Beth wasn't always great but with the right knowledge, anything can be improved.

She seemed to jump on that statement by stating, "Why does Beth seem happy all of the time? Are you feeding her happy pills or something? Just like that comment about getting her best on her return. That is so not like her, or at least not like the way she used to be".

The truth is there were really a multitude of reason's I could have given for my wife's happiness, but I decided to take a turn down the topic of sex to see where that would end up. "Well Allison, having a wife that's multi orgasmic makes marriage a lot easier." At that point, she sprayed wine everywhere as I had timed my response with a sip from her glass.

"Robert!!! Of all of the responses I would have predicted, that was not one of them."

"Well I'm sure that's not something that sisters discuss. But the fact is Beth has become that way over the years and it really helps our love life."

At that, we took a break to towel off everything from the wine and I started working on the dirty dishes. She watched as I loaded the dishwasher and said, "That has to have something to do with it. I didn't even say anything and you start doing the dishes."

"No, that's just common courtesy, which is important in any relationship, not just a marriage. You made dinner, I clean up. That's a fair trade."

"No, you helped my business and I made dinner, clean up was not part of the deal."

"Sorry Allison, I just can't help my self."

"Is that why Beth is so happy, you can't help yourself from being nice to her?"

"I told you earlier why Beth is so happy, and you blew wine everywhere, remember?"

At that we both laughed. After the kitchen was clean I suggested that I leave for the house as I made my way through the living room heading for the door. Before I made it to the door Allison suggested that I wasn't done yet. When I looked at her, obviously confused, she said, "I still need more advice."

I replied, "Your plan is perfect, your business is rocking, there's no more business coaching you need from me."

"No Robert, I need marriage coaching. I want the kind of marriage you and Beth have and I don't know where to start."

With that I sat down in an arm chair and she settled down on the couch. I thoughtfully paused for a moment before saying, "Ok Allison, I can give you some marriage coaching, but here's how it works. Some of my advice comes from my behavioral work with the university and some of it from personal experience. Either way, in the area of marriage enhancement, we will discuss some sensitive issues. But remember, this is just two professional adults talking about marriage the same way we would discuss business."

"What do you mean sensitive issues?"

"Sex."

"Sex!" she said loudly. "Is that all you guys think about? Is that your answer for everything?"

"No, it's not the answer for everything. But sex in a marriage is just as important as profit in a business. If you don't have the right amount or the right quality, your business, or in this case, your marriage folds."

"Ok Mr. Coach, how much is enough?"

Feeling the wine making me bolder I took a chance, "It's not just quantity, its quality too. Do you both orgasm every time you have sex?"

"Are you serious? He does but I very seldom do. My orgasms normally happen alone."

At that response, I had a hard time concealing what I was thinking. The idea of my beautiful sister in law getting herself off was almost more than I could stand. Taking another chance I asked, "Was that what you were planning after I was gone this evening?"

She was obviously embarrassed by my question but the wine she had been drinking took the edge off her response. "How does knowing the answer to that help in my marriage coaching?"

"I was just trying to get an idea of how dire the situation was. But, don't answer that question because I believe I have the information I need." That pissed her off because she knew I was getting the best of her. I continued, "So John makes no effort to be sure you have had at least one orgasm during foreplay?"

"No, he doesn't."

"How often does he perform oral sex on you?"

"He doesn't."

"You're kidding me! That is one of my favorite things to do to Beth. I've become damn good at it too over the years, which has a lot to do with why she is so happy."

After a long pause I suggested, "Maybe he doesn't do it because he doesn't know how and is embarrassed to say so. Have you considered coaching him though the process a couple of times?"

After she looked at the ceiling for what felt like an eternity, she said, "I wouldn't know what to ask for. I have never had a boyfriend or anybody do that very well."

I looked at her for a moment before saying, "You know, there are books and videos on the subject. Maybe you should do a little research on the topic, just like you would do market research for your business."

"I'm not sure I am comfortable looking for that kind of subject matter."

"You could find it online in the privacy of your own home."

"I wouldn't know where to start."

"You could ask Beth about it."

Looking shocked, she said, "This is embarrassing enough having to talk about it with you. That last thing I want to do is talk to someone else. We wouldn't be having this conversation if I hadn't had so much wine."

"Well, those ideas aren't ideal anyway. And if you want to get this taken care of without getting any other people involved and without taking the time for research, there is only one answer and neither one of us have had enough wine to talk about it."

At that statement, she looked right through me before saying, "We have both had a lot of wine and we are just talking as professional adults. This may shock you, but this is just to help my marriage. No one will know about this and this is just for research. There will be no kissing and I will only disrobe enough to serve our purpose, but I want you to perform oral sex on me like you do for Beth."

Oh my God...you could have knocked me over with a feather. But then it really occurred to me what was happening. She was taking control after giving up control all evening. She was also not considering me her brother in law. That is why she just referred to my wife as Beth instead of her sister like she normally refers to her. What was I to do next? After a pregnant pause, I decided to come back with the same tone of control and lack of emotion that she did.

"Ok, we will use the couch because the bedroom would give the wrong idea. You can just slip down your sweats but you will have to remove one leg so that you can spread out far enough. And, you will need to get a couple of towels to put under your butt because you will get very wet."

At that comment I could see her nostrils flare. She was getting turned on and I had her right where I wanted her. Not missing a beat, she got up and walked down the hallway. She came marching back with one towel stating, "I doubt I will need two." She was challenging me and I was up to it. I told her to get comfortable and relax and she responded, "Look, this is just to show me the techniques so I can coach John. I don't need to orgasm to see how it's done." There she was taking control again, so I agreed.

She spread out the towel on the couch and asked that I turn away for a moment which I did. When she said ok, I turned to see her angled on the couch with her left leg out of her sweats and the remainder of the material was pulled back up to cover her pubic area. As I started to move toward her, she placed her left foot on the floor to spread her legs but she held the sweat suit material in place. Sensing her apprehension, I took a mater of fact tone and said, "If you don't mind, I will tell you what I am doing to help you when it comes to coaching John. Fair enough?" She nodded.

As I kneeled down on the floor in front of the couch, I started massaging the top of her knees and her thighs while I spoke, "Normally, when we are to this moment, Beth would have received a foot rub, a shoulder massage, or a hot bath to help start the relaxation process. We would have made out for a bit and participated in some other foreplay before coming to this point." As I said this, I kept moving my hands slowly up her thighs rubbing in circular motions. I then started massaging her pubic area and in doing so was moving the sweat suit material around enough that I could see Allison's beautiful pussy. I must have looked hypnotized because she asked, "Are you just going to stare?"

"I'm not staring, I'm admiring. This is an area where you may need to coach John a little. If he dives right in, then he's missing the point. This is a very special part of the female body. It's not just for making babies, as you know. There are more nerve endings in this area than any other part of the body and therefore it demands respect. You don't just run though an art gallery, do you? No, you stop and appreciate all of the art forms. The area I am massaging right now surrounds one of the greatest works of art on the planet. Besides, while I am admiring your femininity and massaging your pubic area, it is feeling good, isn't it?"

"Wow" she said, "I have never heard a speech like that given about pussy before and yes, it does feel good." Now, we just turned a serious corner. I was using terms like butt, femininity and the like to try to keep this non-sexual. But when she used the word pussy, several things occurred to me. The first was that I have never heard such language from her before which meant she was really opening up to me. Second, she was starting to see that I truly knew what I was doing and letting down her inhabitations. And third, she was getting turned on.

I continued to tease her a little, never making direct contact with the prize.. As if she thought I was waiting for an invitation, she reached down and moved the rest of her bunched-up sweat suit out of the way and spread her legs a bit farther. I explained what was about to happen next. "You notice that I am using my thumbs to move your lips back and forth. The tension on the skin surrounding your clitoris helps to stimulate you and get things warmed up. I will now move my face a little closer and start kissing lightly to get you use to the feel of my lips on your pussy."

Robeth123
Robeth123
36 Followers
12