Great Loop Ch. 05


This set of stories are meant to be read as chapters in a book. If you haven’t read the previous chapters of the Great Loop, I recommend you do to better understand the characters.

All characters are fictional. Obviously, many of the place locations are real.


Toronto, what a beautiful city. Vibrant, friendly people. After arriving and getting my boat squared away at the marina and checking in with customs, I walked into the city to stretch my legs and get a bite to eat. I had grown use to the much slower pace of living on the boat and had a difficult time adjusting to the much faster pace of a bustling city. It reminded me of Long Island and NYC. I realized that I didn’t miss it at all. I passed a gym and stopped in to see if they had guest passes. I purchased a weeks worth so I could work out. The girl at the desk looked very attractive, but also very young, so I kept my thoughts to myself. I asked her if there was a men’s clothing store near by because I needed to buy some clothes. Most of the clothes on the boat had become too big for me, so I wanted to buy some jeans, shorts, tees, and a blazer if I should need one in my travels. I found the store she referred me to and made my purchases. I also noted a massage parlor across the street and thought that would feel good at some point.

When I got back to the boat, I put every thing away, collected my old clothes and planned to find a place to donate them. I walked back to the city, found a place to eat before heading back to the boat and bed. Before going to bed, I called Helen, but got no answer, so I left a message.

Tuesday morning, Helen called, “Hey James, Peter and I’ll arrange a party for while you’re here. Will you be here through the weekend?”

“Yup, plan to leave next Monday morning, so I have all week.”

“Great, Peter and I are really busy this week, but we should be able to set something up for Thursday, Friday or Saturday. I’ll call you once everything is squared away. Enjoy the city.”

“Ok, thanks. Talk to you later.”

With that out of the way, I headed for the gym. I hadn’t been in one since I left Long Island and wanted to get in a workout. After a long workout, I showered and thought I would get a light lunch and head back to the boat when I saw the massage parlor and decided to get a massage. Opening the door, I stepped into a room filled with asian girls, none over about 5-0. At 6-2, I towered over everyone. Everyone stopped talking and one said, “Sir, you here for massage?”


“Please fill out this card.”

It was the typical information card.

Richard James

“Second Chance”

City Marina

Etc, etc.

One of the girls showed me to a room with the typical massage table, low lighting, soft music, running water for white noise, told me to undress, lay face down on the table, cover up and she would be back in a few minutes.

When she returned, she started with my feet and worked her way up my body with a lot of attention to my neck and shoulders. Finishing, she had me roll over. She avoided my groin area as she worked up my body. At the end of 2 hours, I was so relaxed that I wasn’t sure I could even stand up. I felt great and wonderfully relaxed. I left her a generous tip and thanked her as I left. I wondered what would have happened if I had tried to seduce her. She and her associates where certainly attractive in their own way.

I wandered around the area seeing the sites before heading back to the boat. I grabbed a book, poured a drink and settled in for a quiet evening.

“Mr James?”

Looking up, it was the asian girl that did my massage and a friend.


“We come aboard, and finish massage? We not allowed to do a whole body massage at shop, so we come to your boat and finish.”

“Sure, come aboard.”

“You show us your bed, we finish massage.”

As I lead the way, they were talking in their native language and giggling. I was pretty sure I knew where this was going.

As I entered the bedroom, one began undressing me while the other began undressing herself. When I was naked, she indicted that I should lay down on my back and than began getting undressed. With both girls naked, I was surprised that both had bare pussies. Don’t know why I was surprised, but I was. They both started at my toes and feet and worked their way up my legs. This time they did not avoid my groin, but attacked it with their tongues, mouths, hands and bodies. They both ran their tongues up and down my cock and took turns engulfing it. While one was sucking my cock, the other was playing with my balls and ass. As this was going on, one turned around and presented me with her pussy and ass. I couldn’t get my hands on them quick enough. I slipped a finger in her pussy and then a second. My other hand squeezed her ass cheeks and teased her rosebud. This brought some excited chatter and giggling, but they didn’t miss a beat as they continued to massage my cock and balls. As I got gaziantep bayan escort close to blowing my load, everything stopped, they sat up on each side of me, reached across and started kissing and playing with each others pussy and tits. I seemed to get even harder and bigger than I had ever felt before. After about a minute or two, they returned to my cock and started doing the same dual blow job. This time the other girl turned and presented her pussy and ass to me. Once again, I stuffed fingers in her pussy, played with her ass cheeks and rosebud.

I started to use my Tantric sex skills to hold off coming. What they were doing to me was most enjoyable and I was in no hurry for it to end. At one point, one sat down on my cock and started bouncing on it in a cow girl position while the other sat on my face. As I was eating her pussy I played with both their tits and nipples. This also brought some happy chatter and giggling. The girl sitting on my face was getting close to cuming and pressed herself down harder on my face. She exploded and flooded my face with her cum as she rolled off me and curled into a fetus position. The girl riding my cock started bouncing harder and soon she orgasmed hard and rolled off.

As they returned to normal, one looked at me and said, “You no cum?”

“I want more from you before I cum.”

More chatter and giggling and they went back to working my cock. They held hands and stroked it together. Again they used their tongues and mouths. It was getting harder to control myself. I grabbed the girl that sat on my face, put her on all fours and entered her from behind. I leaned forward and grabbed her tits to squeeze as I pumped her pussy. The other girl grabbed my balls from behind and began massaging them. It wasn’t long before I yelled and dumped my load in her pussy. I rolled onto the bed, they both cleaned my cock and each other.

Giggling, one said, “Now, massage finished. Please enjoy your evening.” They dressed and left.

I crawled into bed and promptly feel asleep.

Wednesday morning, I slept in. Getting up, I walked to the marina office, took a shower, dressed and prepared for another day of exploring Toronto. I got a cab and went to the Hockey Hall of Fame. Turns out that it is both a hall of fame and a museum that uses all the latest technology and simulators to give you a chance to play a game with NHL players as well as view playoff games and see memorabilia. I spent the entire day there and even played a simulated game of hockey.

I got back to the marina at dusk and found a place to eat before returning to my boat. No massage girls showed up tonight.

Thursday morning, the phone rang just as I was dressing for the day.

“James, Helen. How are you? Enjoying your stay in our city? We are having a party Friday night at our condo. It will probably last thru most of Saturday as well. I got you two tickets to a show up in the theater district tonight and am having a friend pick you up about 5 this evening to take you to dinner, the show and spend the night with you. You’ll like her a lot. She’ll spend the day with you tomorrow and then bring you to our condo tomorrow evening for our party. Is all that ok with you?”

What could I say? “That sounds great. See you tomorrow evening.”

I wandered back into the city and found a used book store. I had gotten into the habit of reading now that I wasn’t working so hard and enjoyed looking for interesting books in used book stores. Once read, I usually sold them back to a store when buying more. Most of what I read is non-fiction, but occasionally, I do enjoy a good mystery. I found a couple of interesting books about Frank Lloyd Wright and headed back to the boat. I had an hour or so before my date would show up.

After glancing through the books, I changed clothes and put on a new pair of slacks, a shirt and got out the blazer so it would be ready to go. As I was finishing, I heard, “James?”

Looking out, the whole world stopped. I froze with my jaw hanging open. I was speechless. There stood the most beautiful woman in the whole fucking world. I lived on Long Island and had seen many beautiful women, but this one damned near knocked me overboard. Blond, tall, sexy, legs, curves, green eyes, she blew me away.


” Yes, I’m sorry. Damn you’re beautiful. Please come aboard.”

“Thank you. I’m Lori, Helen sent me to take you to dinner and a show tonight. Do I have the right James?”

“Even if I weren’t, I would say yes, but yes you have the right James.”

Even her laugh was sexy as hell. I thought that no woman has the right to be that beautiful and she is going to be with me tonight. Fuck yes!

“Great, we need to get going so we have time for dinner and can get to the show on time.”

“Let me grab my coat and then I am ready.”

We walked up the dock together. She must have been about 5-8, but with her heals, she was almost as tall as me. I wished I was walking behind her so I could watch her ass, but we were walking next to each other.

“Helen told me about your night on the boat and the other three from Watertown. That sounded like fun. Helen and I have been friends for quite a long time now, we met in college and have shared a lot of trouble, boy friends, husbands, etc. My husband is out of town for a few weeks and when she asked if I would show you a good time, I was more than happy to help out. How’s your trip going?”

“It’s going great. I’ve met a lot of interesting people and seen some great places, had some terrific food, lost some weight and generally enjoying my self.”

We arrived at an Audi A7. A sexy car for a sexy woman. As she got in, her dress rode up her legs and revealed an awful lot of thigh and the tops of her thigh highs, but she made no attempt to adjust her dress. She just looked at me and smiled.

“Hope you like Thai food. Helen has made arrangements for us at a local Thai restaurant including ordering for us. It should be an enjoyable dinner.”

Dinner was great, the conversation non-stop. The show was awesome, I got an awful lot of jealous looks from many of the men when they saw Lori. She knew a few members of the audience and acknowledged them with a smile and a nod.

We got back to the marina around 11:00. As we got out of the car to walk to the boat, Lori said, “Just a minute, I’ll get my bag.”

It was true. She was planning to stay with me for the night. She hooked her arm thru mine and we walked down the dock or actually she walked, I floated.

At the boat, she turned, put her arms around my neck, stared into my eyes, smiled and said, “Helen says you may be the best we’ve every had, but she wants a second opinion.” With that she kissed me. The kiss lasted forever. When we broke, we caught our breath and I led her to the bedroom. Turning her to me, I kissed her again. This time our tongues danced together and my hand dropped to cup her ass while my other hand lightly danced across her ear and neck. She pressed closer to me and ground her pelvis against my very hard cock. Our kiss broke and she smiled again as she leaned in for more. Again our tongues danced, my hand rubbed her ass, I played with her ears and neck and she ground her pelvis hard against me.

“Now turn around so I can un-zip your dress.” As she turned, her breast rubbed against my arm. When she had her back to me, she kicked off her shoes. As I was lowering her zipper, I nibbled on her ear, kissed and tongued her neck which drew a nice MMMMMMM. With the zipper un-done, I reached around and cupped her breast while I continued to tease her ears and neck. I slowly pulled her dress off her shoulders to reveal a red lace bra that matched her red dress. As I continued to lower her dress, I kissed her arms and back and found some of her erogenous spots that brought another mmmmmm and revealed a matching pair of red boy shorts. She gracefully stepped out of her dress and I laid it carefully on a chair. At this point, I took off my shirt and pants as erotically as I could. She laughed as I did. Now I was in my boxer briefs only and my excitement was obvious. I ran my hands up her legs, over her ass, along her back to her neck and pulled her in for another kiss. As we were kissing, I unhooked her bra. This brought another mmmmmmmm. Pulling the straps off her shoulders, I stepped back and slowly pulled her bra down her arms revealing her breast. I stepped back even further to admire her. She watched me as I did. Her breast were gorgeously beautiful, standing firm, with highly erect nipples. I tore my eyes away, looked her in the eye and said, “Awesome!” She smiled and laughed. At this point I stepped behind her again, cupped her breast from behind, kissed and nibbled her ears and neck. Her head laid back on my shoulder revealing all of her neck and I kissed it all as I played with her breast and nipples.

Laying her down on the bed, I began with her feet. I sucked on her toes and rubbed her ankles. Working up her legs to her knees with both my hands and my lips I was getting a very steady mmmmmmmmmmm. I continued on up her legs over her thighs to the tops of her stockings. I took my time and rolled both down her legs and off. I returned to her thighs and proceeded up to her pussy. As I touched her panties, I heard a very soft, “Oh fuck, so good.” Her boy shorts were soaked. I reached for the waist band and she lifted herself off the bed so I could pull them off. Her pussy was beautiful. A little landing strip, engorged labia, and shinny with her juices. Her clit was very pronounced and seemed to demand to be licked and sucked, which I promptly did. She had a small orgasm and said, “So good, don’t stop.”

I had no intentions of stopping. I was going to pleasure this woman until she passed out.

Starting at her belly button, I kissed and licked my way up to her breast where I licked, bit, kissed, sucked, pinched, pulled, rolled and loved her nipples. When I finished with one breast, I moved to the other. While my mouth and tongue were busy, I lowered my hand down across her mound, rubbed her clit before inserting two fingers into that beautiful, wet pussy. Curling my fingers up, I quickly found her G-spot and she said, “Oh shit, here it comes!” As she came, one of her hands held my head against her breast while the other held my hand deep in her pussy. When she relaxed, I started kissing my way down her belly to her clit and when my tongue hit her clit and I sucked it into my mouth, she came again.

“Oh oh oh oh oh, fuck, don’t stop. Please, I need your cock, I need it now, please.”

She tried pulling me up by my ears as she humped against my face and chest. Remembering how Holly liked it slow, I slowly worked my way up to kiss her luscious lips. As I did, I slid my cock slowly in her sopping wet pussy. She started humping against me and came again. I put her legs over my shoulders and started pounding her as deep and fast as I could. Her eyes opened and she stared at me, but I could tell she wasn’t seeing anything. Just as she was ready to cum again, I pulled out to a painful, “NO!” Rolling her over and lifting her ass up so I could enter from the back I returned to pounding her pussy.

Each time I pushed in, she said, “OH FUCK, OH FUCK, OH FUCK.” I picked up the pace driving as deep as I could, moistened my finger stuck it in her ass and we both went to the stars on the orgasmic express. I dumped a load of cum in her pussy as we both fell to our sides on the bed. She was passed out. I held her close and after a few minutes her pulse slowed, her breathing slowed, her eyes fluttered open and a slow smile spread across her face. Then we kissed.

“I can’t stop smiling. I’m still on a high. That was sooooo good. I can’t believe I passed out, I’ve never done that before. Helen may be right, but I need more data points!”

The next morning, Lori got a text from Helen, “Well, was I right?” Lori showed me the text and sent back, “Maybe, need more data!”


We walked up to the showers and showered together. Of course I took advantage of a wet and slippery shower to enter her again and drove her to another orgasm. I wonder what the person in the other shower thought when Lori screamed in pleasure.

Lori took me to various art galleries and a museum. I wanted to go back to the Hockey Hall of Fame, but she had been many times and was more interested in showing me the art collections of Toronto. We returned to the boat around 4:30 to get ready for Helen’s party. She shimmered out of her clothes and into a little sundress thing that barely covered her ass and revealed a lot of cleavage.

“Nothing is going to stay on long, and the small stuff gets lost, so most of us ladies don’t wear underwear and neither do the men.”

Climbing into the A7, she flashed me her pussy and let me run my hand across it. That got another mmmmmmm. It was only a 10 minute drive to Peter and Helen’s building. They had the entire top floor. After the elevator door closed, Lori stuck her arms in the air and said, “Will you please do the honors?” I pulled off her dress.

The doors opened. Everyone in the room (probably 12 or 14) were naked and Helen was being serviced by two men. A couple of women were in a 69 on the sofa and others were watching, having a drink and chatting.

Lori said, “Get your clothes off and put them in there.” Pointing at a closet.

The condo was huge, being the entire top floor of the building. Windows were floor to ceiling with no drapes. I wondered if the neighbors in the near by buildings were enjoying the show. Furnishings were very sleek and modern with lots of chrome and leather. A beautiful place for a party.

Helen saw us, “James, welcome. I like your beautiful cock, bring it over here so I can welcome you properly.”

While she was sucking my cock, Peter walked in “Hey Mate, good to see ya. Hey everyone, this is the bloke I was telling you about, say hey to James!”

Lori leaned over and whispered, “Have fun, I’ll see you later. Save some for Helen and I. We’re going to do you together later.” and walked off with a guy.

As I stood there, a very striking dark skinned woman approached, “Hi James, I’m Ann. Welcome to the party. Helen has been telling us all about you. She’s right, you have a beautiful cock.”

With that, she dropped to her knees and engulfed my cock. I quickly realized that if I didn’t slow down I would be done very soon. I pulled Ann up to me and suggested we find a place to sit or lay. We found a wide chair and cuddled up in it. Ann sat on my lap and put my cock between her ass cheeks. Since she was already naked, I focused on her tits and pussy. It wasn’t long and she was mewing as I licked her neck, pinched and pulled her nipples and teased her clit. She was wiggling her ass all over my cock. It felt strangely good, but I knew I wasn’t going to enter her in this position, so simply enjoyed it. After several minutes of playing with her clit she screamed, “FUCK, I’m cuming, FUCK, FUCK, FUCK, YYYYEEEESSSSSSS.” When she finished she said, “Oh you darling man. I hope I get another chance with you tonight.”

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