Great Loop Ch. 01

"Ok, do what you were doing, but insert your fingers in my pussy and then curl them up as if to invite someone to come closer. Also turn around into a 69 position, you do know that position?"

We got going. She was sucking on my dick, playing with my balls. I found what I assumed was her clit and did what she told me to do with my fingers. When it all came together, her ass came off the sofa and she started bouncing. She pulled off my dick and kept saying, " Yes, yes, yes. Oh good, your'e doing very good, don't stop." Her bouncing stopped and she seemed to freeze. She must have had an orgasm because my face was flooded with her juices. She grabbed my dick and started pumping and sucking. My balls were churning, I told her I was coming, and she just sucked harder. I came harder than I had ever come. Nothing leaked out of her mouth. I turned around and kissed her as hard as I could. I had never given a woman an orgasm or come so hard.

"Shit, is this what its all about? Fuck, I wish I had known this years ago. This is so good. Yeahhhhhh!"

Holly was laughing. "Yes, that's what its all about. We aren't done yet. There's still a lot more for you to learn. Monday, same time?"

"Fuck yes!"

I had parties to cater Friday night, Saturday and Sunday. Fortunately, I had Jean and Lois because my head wasn't in the game. All I could think about was 1:00 Monday.

The elevator opened and Holly was standing there fully clothed with her arms open. I stepped into them and gave her the most passionate kiss I had ever given anyone. She returned the kiss.

"Whoa, have you learned that lesson well!"

"Today, we focus on how to undress a woman and how you can make that sensual. Some women like to have their clothes torn off, others like to be undressed. Tearing clothes off is easy, undressing takes some practice. I like to be undressed. Slowly."

"You mean, we're not going to fuck?"

"Jim, like I said, you have a lot more to learn, but yes, we'll get to fucking." She laughed.

"Now, step behind me. You remember how to use my neck and ears to start turning me on?"

"Yes."

"Get to it. As I start to warm up, start rubbing and cupping my boobs through my blouse. Then start to unbutton my blouse."

I did as she told me. I could feel her getting excited as I kissed and nibbled her ears and neck. Slowly, I began to play with her boobs and then to unbutton her blouse. The more skin that was exposed and that I could feel, the more excited she seemed to get. Her blouse slid to the floor revealing a lacy white bra.

"Now you have a choice, what do you think is the correct choice?"

"Er, I don't know. Your slacks would be my first guess."

"Actually, at least for me, either the slacks or the bra works, but I think that for most women, the slacks would be the logical choice. That keeps everything covered for a few minutes, keeps the allure alive."

I reached for her slacks, "Don't give up on my neck and don't forget my shoulders and upper arms as you work down my body. Lighter, remember, as light as possible. Just a brush of your lips and finger tips. Your hands should slide down my arms from my shoulders to get to my slacks. Always try to stay in touch with my body without tickling me! You can also continue to run your fingers over my boobs and nipples as you move down."

Moving my hands to her shoulders and my lips to her neck, I started again. My hands slowly descended down her arms and then back up. I remembered some erogenous zones and made sure to include them. I also ran my finger tips over her nipples. A little moan escaped her. I continued down across her stomach as lightly as I could. I probably tickled her a little but I continued on. Getting to the waist of her slacks, I unbuttoned them and slid down the zipper. I was going to continue down, but returned to her nipples and brushed them for a few seconds.

"Yes, very good...ahhhh."

Returning to her waist, I slipped my fingers inside the waistband and moved them around to her hips and slowly started to slide them down over her ass and then her thighs. I remembered that the ass is erogenous as well, so brushed my hands and fingers over that as well. I must have done well, because she pressed against my hands and moaned a little louder. Remembering the different zones and spots on her legs and knees I made sure to touch each as I lowered her slacks to the floor. She stepped out of them very gracefully. My hands retraced their way back up her legs and ass to her shoulders.

"YESSSS, very good, keep going. Your'e doing vvveeerrryyy well."

Kissing her neck and ears, my fingers slowly traced the out line of her bra as I moved toward the clasp in back. Without releasing the clasp, I ran my fingers around on the underside of the straps. Working my way back to the clasp, I gently released it and let the bra just hang as my hands followed the straps up her back and to her neck. I brushed her ears, blew gently on them and lifted the straps off her shoulders. Slowly her breast were exposed as I lowered the bra. They were magnificent. I also noted that she was breathing a little harder.

Pausing, I gathered my thoughts on what should happen next. She waited patiently. I returned to the ears and neck briefly before allowing my hands to capture her breast and hold them While kissing her shoulders, her nipples caught my attention and I began to roll them, then brush my hand across them, pinched them a little and extended them.

"VVVEEERRRRYYYY good. Doing fine, don't stop." I spent several minutes teasing and playing with her breasts. Returning my hands to her shoulders, I started down her arms to her panties. I ran my hand over her ass, then across her mound. She humped my hand once. I slipped my fingers under the waistband of her panties and slowly worked them down being sure to touch all her hot spots. Again, she gracefully stepped out of her panties which I noticed were wet.

She sat back on the sofa, spread her legs a little and said, "Jim, its time for you to get undressed."

My clothes hit the floor in about 2 seconds. She laughed, "You should be able to do that a little more erotically, but I understand your desire. Now use your tongue on my legs and pussy again."

I was hard as stone. I hoped she didn't leave me hanging today. I returned to using my tongue on her feet, legs, knees, thighs and finally her pussy. She was really wet. As I slipped a finger in her pussy and licked her lips, a loud moan escaped her and she was making little humping motions before pulling my head tight against her. I continued to lick and found her g-spot.

"Yes, Yes, Yes, do it! Make me cum. " Off she went for a ride thru the stars. I laid with my head on her stomach as she came back down from her high. As her breathing returned to normal, I stood, she grabbed my ass and pulled my cock to her mouth. I watched as it disappeared. She was doing some wondrous things with her tongue and throat and I could feel it coming. Again, I exploded down her throat, she didn't spill a drop. I had to grab the back of the sofa to keep from falling.

After catching our collective breaths, I sat down next to her and she leaned over and kissed me with a lot of tongue. I could taste myself on her tongue. That was a new experience.

"Jim, you are becoming my favorite client. You're catching on exceptionally fast and I look forward to your visits. Next session, will be some situations you may find your self in and how best to handle them. I hope you enjoyed our time together today. Now, you need to leave so I can prepare for my next appointment."

"Thank you. I did enjoy today. I was amazed that I could make you respond as you did. Is that what I can expect every time?"

"Well, not every time. Every woman is different and will respond differently and will have their own little likes and dislikes. You will learn to read the signs as you go thru relationships with women. Now get dressed and go."

While I was attending sessions with Holly, I had not forgotten Ben's admonition that I may not live to 60. I continued to work out. I was losing weight, hadn't smoked and was eating healthier. I also spent less time in the office and let Jean and Lois take on more responsibility. I still hadn't figured out what to do about a vacation, but my sex life was definitely getting better.

I started thinking about sailing my boat to the Bahama's or something like that. Then I thought about a cruise, but that didn't interest me. I happened to pick up a boating magazine that had an article about the Great Loop. Basically, this is a water route around the eastern half of the United States. It runs up the intracoastal waterway (ICW) to New York, then up the Hudson River, across the Erie Canal to the Great Lakes, down Lake Michigan to Chicago, by river to the Mississippi River, down to the Gulf of Mexico, to Florida and back to the ICW. It started me thinking about how I might do the loop.

The next session with Holly was great. She greeted me wearing a robe that quickly revealed she had nothing on underneath. We kissed, I disrobed her and myself (in a more erotic manner) and then it was time. She led me to a bedroom and laid back on the bed. I started by kissing her and using everything I had learned about erogenous zones to get her excited. Finally, I was sucking her clit and playing with her pussy. I was hard as stone.

"Ok Jim, time to enter me. If the sex is heavy and raw, you can just enter a woman if she is lubricated, or you can enter slowly and gently. I prefer the latter. It gives me a chance to adjust to you and enjoy the pleasure the I derive from your entry."

I entered her slowly as I could. She was wet, tight, and like velvet. When I bottomed out, I began to stroke her, "No, not like that. Slow down, use long slow strokes. Use the length of your cock to give pleasure. Remember, giving pleasure gets pleasure. If I want it faster or harder, you'll know. Now suck on my nipples as you slowly stroke in me."

"MMmmmm, much better."

I slowed down and suckled her nipples. Finally thinking a little better, I moved to kiss her and then to her neck and ears. She wrapped her legs around my ass and pulled me deeper. That felt good to me!

"Don't stop with the kisses, but now would be a good time to go faster and a little harder but still use a full length stroke."

I sped up. "YES, good, so good. Here I cum." and she had a small orgasm. "Don't stop, keep going, harder, faster."

Her legs came off my ass and her ass came off the bed raising me as well. She was panting, holding that position, when she froze, screamed and went on an orgasmic ride and took me with her. I pumped an awful lot of cum into that beautiful pussy. As we slowly returned to normal, she looked at me, "That Jim, is what can happen when you focus on your partners pleasure!"

I kissed her and kissed her as I started pumping again. She put her legs over my shoulders and it wasn't long before we climbed the orgasmic peak again. This time we separated and I began to laugh, a deep belly shaking laugh and Holly joined me.

"This is the best afternoon of my life! You are wonderful, beautiful, magnificent, stunning."

Laughing, "Jim, you have come a long way, but you still have more to learn, and now it's time for you to go."

Both Jean and Lois had noticed a change in me. I seemed less driven, more relaxed and looked better. They both commented on it. Lois said, "You must be getting laid regularly. It's good on you." They both laughed.

I did more research on The Loop as I began to call it. I became excited about it. It wasn't something that could be done in a week or two. Some people try to do it in a year, others may take 2-3 years to complete it. I also learned that my boat was not appropriate for that journey.

My sessions with Holly continued. She taught me different positions, we talked about threesomes and more somes, she also taught me some of the basics of Tantric Sex and made me practice them so that I was delivering shattering orgasms to her. My tenth session was on a Wednesday. I went thru the entire skill set that I had learned, beginning with a kiss and hug, erogenous zones, oral sex and a variety of positions. While Holly was on all fours and I was pounding her from behind, "Jim, when you sense I am about to cum, I want you to insert a finger in my ass. Lubricate it with my fluids first and enter slowly, so I adjust." She started breathing harder, her head was back, and she was making mewing sounds. I knew she was close and so was I. I rubbed my finger along my dick to lube it and then slowly pushed it in her ass as I was driving my cock in her pussy. Her orgasm had fireworks that blasted us both to the stars. That may have been the hardest I'd ever cum. I held her close as we caught our collective breaths and our heart rates returned to normal.

"Congratulations Jim, you've graduated. I'm sure you'll be able to please any partner you have. I've enjoyed working with you and teaching you, but this will be our last session."

"Huh, I'm not ready yet, I have more to learn. Surely you have more to teach me. We can't be done yet."

"Jim, when we started these sessions, you knew that I would determine when you were done. I'm sorry, but I have nothing to teach you that you can't figure out with a partner on your own. I know this is difficult, it is with most of my clients, but that's how it is. I have prepared a final report for the doctor. I'll also tell you that I have enjoyed our time together immensely and I'll miss our sessions together. Now it's time for you to go."

"Can I take you to dinner or a show?"

"I'm sorry, but my policy is I don't socialize with any of my clients. A different time, or place, or circumstances and I would enjoy going to dinner with you, but as a client, that is impossible."

I kissed her as I left and when the door closed behind me I felt lonely.

The holiday season is my busiest time of year. We frequently have more than one party each day. We have to staff up, hire extra servers, rent trucks and vans, order food, and all the associated details that make our service so respected. Jean, Lois and I were putting in long hours, frequently 12-14 hours a day. I occasionally still slept on the sofa in my office, but I tried to limit that to only once or twice a week.

As expected, Jean and Lois made everything go smoothly. When the unexpected occurred, they handled it with a smile and a laugh and after our last dinner on January 2, we collapsed and swore to sleep for a week. I actually took a few days off from work. Jean and Lois called to make sure I was alright because it was so unusual for me to take time off. I spent that time researching the Loop, the type of boat I would need, places to visit and many other elements of The Loop. I decided to sell my sail boat. I hadn't really used it in years and it wasn't what I needed if I did do The Loop.

I called a friend of mine that runs a marina and has a boat brokerage. He agreed to list the boat. He thought it would probably take 4-6 months to sell because it was only January and boats aren't high on anyones list at that time of year on Long Island. A few days later I dropped by his office to sign the papers and turn over the keys. He introduced me to his new assistant, Debbie, and then I signed the sales contracts and other documents. We got to talking about The Loop and he asked me if I planned to sell my business or just turn it over to someone to run. I hadn't made any decisions along those lines and told him so.

"Hey Boss, I'm going to lunch. Can I get you anything?"

"No thanks, Jim?"

"No, I'm going to get going. I'll stay in touch. Hey Debbie, can I join you for lunch?"

"Sure!"

We had a nice lunch. Conversation was easy, she was easy on the eyes with a nice figure, pretty eyes and an awesome smile. I told her about The Loop and she was jealous. She loved boating, the water and everything associated with it. As we were leaving, "Debbie, I have two tickets to an Islanders game tomorrow evening. You interested?"

"I'd love to."

We exchanged phone numbers and I promised to call her and get her address so I could pick her up.

We had a nice quiet dinner and got to the game half way thru the first period. She got into the spirit of things right away, asked lots of questions about hockey and the rules and enjoyed the game. The Islanders won.

Walking out to the car, she put her arm thru mine, put her head on my shoulder and said, "Jim, I've had a wonderful time tonight. Would it be too forward of me to say I'd like to go back to your place for the night?"

"Are you sure?"

"I haven't had such a great evening or met a nicer man in the last few years. Yes, I'm sure."

Once home, we kissed and I started remembering everything I had learned from Holly. We shared tongues, I explored her erogenous zones, undressed her. Before the night was over she had ridden the orgasmic express several times before I joined her. As we lay recovering, she flashed that beautiful smile and said, "Whoa, wow, how did you ever learn how to make love like that? No, don't tell me, but I've never experienced anything like that. I think I'm in love."

The next morning, we showered together and made love again. Dropping her off at work, she leaned over, kissed me, and asked when we could see each other again. "I'll call you tonight and we can set up a date."

"Just lead me to your bedroom." She laughed as she got out of the car.

Back at the office, I turned on the computer and went directly to my files for The Loop. Jean stuck her head in, "Hey Boss, are we going to have our usual post party review today?"

"You and Lois can do it without me. You know the process."

"Boss, are you alright? We've been doing these weekly for 15 years and now you're opting out? What's up with you?"

I told her about The Loop.

"You should do it. Lois and I can run the business. We do mostly now and you would only be a phone call away. Yes, do it. You could use a nice relaxing vacation, and if it took you a couple years, so what."

At that moment, I decided to do The Great Loop!