Great Loop Ch. 01

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Earning to give pleasure.
7.1k words
4.66
25.7k
24

Part 1 of the 16 part series

Updated 06/08/2023
Created 06/26/2016
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All characters are fictional. Obviously, many of the place locations are real.

*****

"Ok Ben, give it to me straight. How bad is it?"

"Jim, you're 30 pounds over weight, your blood pressure is sky high, your good cholesterol is low , your bad cholesterol is high, and your triglycerides are high. You are border line diabetic, your creatinine is high indicating your kidneys may be going bad, you smoke and that is just the beginning. If you don't have a life style change, you won't live to be 60. How long has it been since you had a vacation or even got laid?"

Ben and I had known each other since he hired me to cater his oldest daughters wedding. Two more daughters weddings and we became friends. Ben is an ER physician at a local hospital and has a very small practice on the side. I hadn't felt well the past few months and finally went to Ben for a physical and check up. Obviously, the news was not good.

"I went sailing last year for a few hours and some girl gave me a blow job maybe 10 years ago. Does that count?"

"No, I mean when did you take a week or two off from work and forget about everything? When did you spend time with a woman and fuck her silly and get off?"

"I can't remember, maybe when Janet and I were still married."

"Jim, you've been divorced for over 15 years. What's the matter with you?"

I shrugged my shoulders.

"Ok, here's the deal. I want you to get a gym membership and start working out. One of your chef's can put together a menu for you to eat that is healthy. You have to quit smoking. I want you to go home every night and get 8 hours of sleep in YOUR bed, not the sofa in your office. I want you back here in two months and you better have lost a minimum of 10 pounds and not had a cigaret. If you don't, I'm going to kick your ass so hard, you won't be able to sit down for a month. Can I be any clearer? I'm going to give you a script for some blood pressure medicine. Get it filled and take it. We need to get that down so you don't have a stroke and to prevent heart disease. Jesus, you're only 40 years old and look like your 60."

Leaving his office all I could think was I won't live till I'm 60 and I need to get laid. Those two thoughts haunted my sleep, on the office couch, for the next week.

I woke up one morning with chest pain. That scared the shit out of me. The ER said it was indigestion and gave me some pills. I quickly found the scrip that Ben had written for BP medicine and had it filled. I also joined a gym, met with a trainer and started working out.

I own a major catering business on Long Island. Most of my work is weddings, corporate events, and political fund raisers. We're good at what we do. My staff is loyal, drug free due to random drug testing and my chef's are graduates of the Culinary Institute of America (CIA). I have a manager (Jean) and an assistant manager (Lois) that help me keep everything running smoothly. We've been together for almost 15 years. Both are married, have kids and are hard workers. Even with all this help, I can't sit back and let them do their work. I have to be involved. As a result, I work 15-16 hours a day and often sleep in my office. I don't really have any outside interest, although I do have a sail boat that hardly ever gets used. I do occasionally go out with a girl, but as I told Ben, it hasn't resulted in any sex.

The trainer took photos of me from the front, both sides and the back as before pictures. We met every morning at 6:00 and he worked me hard. There was a woman that came every day also to work out. She was attractive and I guessed she was in her mid-30's. I kept remembering Ben's words. "You won't live to 60 and you need to get laid."

I was working on the living to 60 part, but not the getting laid part. I finally worked up the courage to introduce myself to this woman.

"Hi, my name is Jim. We seem to be the only ones that like to work out early."

"Hi Jim, I'm Carol and I think you're right."

We were both sweating and wiping ourselves with a towel. How romantic is that?

"I usually go get a light breakfast after my workout. Would you care to join me?"

"I would love to. Let me shower and I'll meet you in the lobby. I have a 9:00 appointment so I won't be able to take a long time."

Over a light breakfast we exchanged information about ourselves. She was a model, well not in the sense you think of a model. She was an eye and hand model. If you see an ad in a magazine that is someones eyes or hands, it may be Carol's eyes or hands. She had a photo shoot of her hands that morning, thus her 9:00 appointment.

Slowly, we became more comfortable with each other. I said to myself, that after I lost 5 pounds I was going to ask Carol to go sailing with me for a day. I lost the 5 pounds and watched the weather forecast for a good day. Finally I asked Carol if she wanted to go sailing on Thursday. She agreed.

We had a wonderful time. Returning to port, we docked the boat, and went to dinner. We got back to her apartment and she invited me in. We kissed, hugged and soon I was playing with her boobs. We got undressed, kissed some more and got into bed. I crawled on top, put my dick in her and pumped until I came. I rolled off and fell asleep. I woke about an hour later. Carol was up and had a robe on. She thanked me for a nice day, showed me the door and I left.

The next morning, we finished our work out and she joined me for coffee.

"Jim, you're a nice guy. I really like you, but you are a lousy lover. Its like you're a 16 year old or something. You play with my boobs, climb on me, pump a few times, get off and you're done. You have no consideration for your partner and her pleasure. I'm afraid that I don't want to date you again. I'm sorry, but thats that way it is." She stood up and left.

No one had ever told me anything like that. Now what? I had an appointment with Ben in a few days. He'll probably laugh his ass off when I tell him what she said.

Ben wasn't happy with my progress. He suggested a low carb diet to take the weight off faster. My BP was down a bit and I hadn't had a cigaret in a month. When I told him about my date and what Carol said, he laughed. He said I needed lessons!

"Jim, there's a licensed sex therapist down the hall. She isn't taking any new patients, but she owes me a couple of favors. If you want, I'll see if I can get you an appointment."

"Huh,...?"

"Well, do you want an appointment?"

"Yeah, I guess so."

I walked out of Ben's office with an appointment for Friday at 3:00.

Friday, 2:45, I stood outside the therapist door:

Dr. Susan Lindquist

Licensed Sex Therapist

Taking a deep breath, I opened the door and stepped into a well appointed reception area. The receptionist was an older woman.

"Yes? Are you here to see Dr. Lindquist?"

"Yes, I have a 3:00 appointment."

"Fill out these forms and the doctor'll be ready for you in a few minutes."

Completing the forms, the inner office door opened:

"Jim, please come in."

I don't know what I expected, well I do know, but what I saw wasn't it. She was about 50 years old, a few extra pounds, a wedding band on her hand, pictures of kids on her desk, well dressed and manicured. There was no bed in the office, just a few chairs, a sofa and her desk.

"Please sit down. Ben tells me your'e having some problems with your sex life and would like some help. Please tell me what's going on with you and perhaps I can offer some help."

I explained that I had divorced 15 years ago, had not had a sex life and that Ben said I needed one. I also told her about my date with Carol and what she had said to me. I found her easy to talk to.

"Your problem is not uncommon. I see quite a few couples where the male has similar problems and the couple is looking to change their sex life before it ends in divorce. I must admit, you are the first single male I have seen seeking help."

"Men often don't understand that they can have the best sex of their lives if they focus on their partners pleasure instead of their own. The more they want to pleasure their partner, the more their partner will want to pleasure them. It's a win/win situation. The secret to providing that pleasure is learning what pleasures her and having the skills to deliver that pleasure. Not all woman have the same sexual desires and derive pleasure in the same way. Detecting those desires, short of having her spell them out for you, is a skill that is easily learned. The skill of delivering what she desires can be learned, but takes practice. Since your'e single, I am assuming you don't currently have a partner to help you learn these skills. Am I correct?"

"Yes."

"Ok, let's begin with some reading material that describes a woman's body and erogenous zones and how they affect a woman as well as information about some sex improvement weekends. It'll take you a week or so to get through it all because you'll want to go through it several times. The material includes a couple of suggested web sites that you may want to watch, as well as some hints of what to look for when you are watching. To answer your question, yes, they are pornography sites."

She escorted me to the door, "Phyllis, please give Jim the packet of basic information and schedule him for another appointment in two weeks. I look forward to seeing you again and answering all your questions. I'm sure you'll have many. It was a pleasure meeting you. See you in a couple of weeks."

Two weeks later I was back. She was right, I had a thousand questions. I'd read all the material every night, watched the videos and still had questions.

"Well Jim, did you get a chance to read the material and watch the videos?"

"I read everything every night and watched the videos every night. I still have a lot of questions."

"Ok, great. Let's get started with your questions."

An hour later, most of my questions had some form of an answer, or information about where I could possibly get an answer. I also expressed my interest in learning more about Tantric Sex techniques. She nodded and made some notes. I also expressed my concern about finding someone to help me learn to be a better lover that would have the patience and ability to teach me.

"I can help you with your last concern. Here is the name of a woman and her phone number. She is not licensed and is not a prostitute but does help me out with unusual situations. I spoke to her about you and she's willing to help if you want it. If you decide to use her, she will require a letter certifying that you are free of STD's. Ben can provide that for you. She is expecting a call from you sometime soon."

"Huh, this woman, does she work for you or is she free lance or something else?"

"Let's just say that she has a very high sex drive and is willing to help men and women with sexual issues. She is extremely selective about who she helps. Your first visit, if you go, will be a 'do we have chemistry' type of visit. It usually does not result in any intimacy. That being said, there have been exceptions to that as well. She will provide me with written reports of your progress and she will determine when the sessions are complete. Any more questions?"

"Huh, no. Do I need to come back here?"

"Yes, after you've completed your sessions with Holly, you can call and make an appointment."

...

"Hello? This is Holly, may I help you?"

"This is Jim. I believe that Dr. Lindquist called you about me."

"Yes, Jim, so glad to hear from you. Are you calling to make an appointment? I have an opening Monday at 1:00 if you're available."

"Wow, this is moving fast."

"Were you expecting something different?"

"Er, no, don't know what I was expecting. Ok, Monday at 1:00."

"Good, you have my address. My only request is that you be discrete. I think you can understand."

"Huh, sure, discrete. See you Monday."

I had three weddings to cater over the weekend and didn't have time to think about the appointment.

Monday morning, I considered backing out of the appointment. Then I heard Ben's voice in my head and Carol's comments and thought I'd at least go to the first appointment. Nothing intimate was supposed to happen.

The taxi dropped me off in front of a simple apartment building. It had a doorman that opened the door. "Are you Jim?"

"Yes?"

"Miss Holly is expecting you. She has the whole top floor. Here is the code for the elevator."

The elevator door opened into a large foyer of a beautiful apartment. Holly greeted me with a smile and a short hug.

I guessed she was my age, about 5-5 tall, short blonde hair, blue eyes and nothing revealing about her physique because of the long flowing robe she wore.

"Please, come in. Would you like a glass of wine to help calm the nerves? Everyone is nervous the first time they visit me for a session."

"Yes, thank you."

"Red or White?"

"Red."

"Ok, let's get the formalities out of the way. Do you have a letter certifying you are free of STD's?"

I gave her the letter from Ben. She glanced at it. "Good, now let's get going."

"Dr Lindquist briefed me on your situation. You are rather unusual so I am interested. Tell me about your sexual history."

I started with Janet, my first experience, our marriage and its falling apart. After that there was no experience until my night with Carol. Holly seemed quite surprised that I had so little experience.

"Why do you want to learn these techniques?"

"My doctor said that sex would be good for me. If I find a partner, I would want to make her happy as well as enjoying it myself."

"Your'e not planning on becoming the neighborhood stud?"

Laughing, "No."

"I like you. I'll take you on. Sessions typically run about 2 hours, sometimes longer, sometimes shorter. I like two sessions a week. You know my fee?"

"Yes."

"Good. Then why don't we start. Let's start with a kiss and hug."

"Huh, now?"

"Yes, give me a hug and a passionate kiss."

We stood, stepped to each other and I hugged and kissed her. "Jim, I've had a more passionate kiss from a 2 month old baby. Here let me show you."

She placed my arms around her back as she slipped her arms around my neck. Her lips touched mine and then I felt her tongue pressing to get into my mouth. Parting my lips, she slipped her tongue in and started to dance with mine. After about 30 seconds she backed her tongue out and when mine didn't follow she darted back in to pull my tongue to her mouth. I got the message. Another 30 seconds and we parted. I was feeling a little excited.

"Much better, Jim! A kiss can be very passionate. It tells a woman that you can be a gentle and sexy man. Now we are going to kiss again, and if you think it appropriate, drop a hand down to my buttocks and pull me closer."

We kissed again. This time she pressed her pelvis against mine and did a little rubbing. I dropped my hand to her buttocks. We broke apart, "very good. Now what do you think I was trying to tell you?"

"You're ready to fuck."

She laughed, "No, I'm telling you that I'm interested and wasn't saying no, but I wasn't telling you I wanted you either. I was getting an idea of what your response to me was. Were you getting hard or not."

"Oh. I was certainly getting hard."

"I know. Now kiss me again."

We kissed, she rubbed her pelvis against me, my hand dropped to her buttocks (it felt like an awfully nice ass) and I started to squeeze them. I was also getting hard. We continued for what seemed like forever, but was about 45 seconds. When we separated, she was slightly flushed and I was breathing harder.

"See what a kiss can do. Lips are sensual organs that give and receive information about each other. The brain processes that information and begins to determine if your partner might be a good partner for you. Many kisses on a woman's lips, face and body can be a real turn on for her. Most women like to be kissed. We'll continue to work on that as we progress. Any questions?"

"No, what now?"

"Lets see what my reaction is when you kiss, touch and blow on my neck and ears. Those are erogenous zones and can further turn on your partner. When you are kissing or touching these areas, keep your touch light and blow lightly. You don't want to give anyone a hickey or injure the ear, so be sensitive and go lightly. You can do this from either in front or from behind me. I prefer for my partner to be behind me."

Stepping in front of me, she pulled my hands around her stomach and tilted her head to the side. I started to kiss her neck. "Lighter, lighter, barely make contact with your lips. Much better. Mmmm."

"At the same time, use your fingers on my other ear. Lightly, lightly, good. Mmmmmm. You can add some tongue if you want. OH ya, that's it."

I could feel her turning on. She started pressing her ass against my dick getting me even harder. I was beginning to hope.

Then she tilted her head to the other side. I immediately started kissing and licking on the other side and got the desired response. I was enjoying this. This was fun. It was intoxicating. As I was nibbling on an ear, she pulled a hand up to her breast. I could feel a very aroused nipple. She rubbed my palm over her entire breast then guided me to roll her nipple. I stopped kissing her neck.

"No, no, don't stop. It's all part of the seduction of a woman and I am enjoying being seduced."

I went back to doing it all. She didn't need to guide my hand on her boob.

Stepping away from me, she was breathing as hard as I was, but said, "I'm sorry, but our time is up. You made good progress today. I know you'll have a case of blue balls tonight, but I have another client coming shortly, so its time for you to go."

"What, you're going to leave me like this?"

"I'm sorry Jim, but thats the way it has to be. We will continue with erogenous zones next session. Wednesday, same time?"

"See you then."

Wednesday couldn't get here quick enough.

"Good afternoon, Sir. Here's the elevator code. Miss Holly is expecting you."

The elevator opened, Holly stood there with her arms open. I stepped into them and gave her a really passionate kiss. She returned it. "Very good kiss!"

"Today, we're going to focus on the erogenous zones on the feet, legs, and arms."

Her robe came off and I saw her body for the first time. She was wearing a white lacy bra and pantie set. She was beautiful. I started getting hard immediately.

Setting on the sofa, she leaned back and placed a foot in my lap. She talked me through the zones on her feet, up the back of the calves, her knees and then moved me to her arms all the way to her neck and ears where I continued what I had learned on Monday. Then she made me do the other leg. Every time I did it right, I was rewarded with a "Mmmmmmm."

About an hour into the session, "Jim, why don't you drop your pants. The next elements will require both of us to use our lips and tongue as well as our hands and fingers."

"Now I want you to start just below the knee, focus on the knee and then work up towards my crotch. Without any assistance from me, see if you can hit all my spots."

She laid back and I started with her right knee. Working up the inside of her thigh, I was rewarded with an "Mmmmmm." Continuing, I could start to smell her sex. It was intoxicating. Moving to her left knee, I proceeded to do the same thing. When I got to her pussy, I licked her lips through her panties.

"Yes, ohhhhh, you're doing fine." She lifted her ass off the sofa, pulled her panties down and pulled my head into her pussy. I kept licking as I gently rubbed my fingers up and down her thighs. Pulling my head away, "Take off your underwear. I want to show you how lips, tongue, and fingers can all come together to provide real pleasure."

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