Orgasm Diary September 2020
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Hindsight 20/20 Book 1Chapter 67 free porn video
Tracy must have had trouble deciding what to wear because we were finishing our first mimosa when they finally returned. We were on the couch with Anne snuggled into my lap. They had finished their drinks, and Doug got everyone a fresh round. Anne was in a loving mood, and kissed me often and rubbed her hands on my chest. Tracy was sitting under Doug's arm as they sipped their drinks.
I asked about their schedule for tomorrow, and they replied that it was the last day of the show. They had booth duty from nine until noon, and then they had to fly out around 5 PM. I suggested that they go down at 8 AM to get their bags and bring them up to our room. Then they could check out and go to the show. When they finished, they could come back and change into something comfortable, and then we could go and have lunch before they had to leave for the airport. I thought about offering to drive them, but it's a pain to drive to O'Hare, so I decided to let them take a cab.
They thought it was a good idea, and when we finished our drinks, Anne asked me to show her the view from my room. I didn't resist her request, and told Tracy that I would see her in the morning unless she and Anne decided to share. She blushed and I left with Anne to go to the room. She was looking out the window at the lake while I closed the door. I went into the bathroom and brushed my teeth. Anne came in and started brushing hers while I undressed and hung up my clothes. I met her as I came out of the closet in just my boxers. I closed the blinds so the sun wouldn't wake us too early, and I set the alarm for 7:30. I held her, kissed her softly, and asked what she preferred?
"I'm just ready for you hard and fast. I want you on top and I want you to shove it in me." I led her to the bed and took off her under clothes and as she got into bed, I dropped my boxers. I was not completely hard yet but she saw that it was heading that way. I told her that I loved a woman who knew what she wanted.
I went hard and fast. She said I was as big as she ever had, but it felt good to have a young hard cock fill her up. We both came within a minute of each other, and I laid back on the bed so I didn't crush her by lying on top of her. She went down and took my semi-hard cock into her mouth, which made me glad that I was not with a yucky, gross little girl. I was hard soon enough and she climbed on for round two. I had just cum and she now had more control of the situation. She came three more times before I shot off my second time forty minutes later. I asked if she wanted to go for round three, or take a break and shower. She voted for the shower so we cleaned up. After we finished, she headed for the bed and I told her I would bring her a drink.
I walked into the living room naked after I peeked out and saw that Doug and Tracy weren't still on the couch. I went to the fridge and took out some ice, OJ and champagne. I started to put some snacks on a plate and while breaking off some grapes, I heard Doug's door open. I looked over to see Tracy in a robe closing the door behind her. She saw me standing there and she stopped.
"Is is time to share and trade places already? We have only finished round two."
"Well, your buddy fell asleep after round one."
"I'm sorry. You should have kept him away from the hard stuff, as he's a lightweight."
She was looking down at my cock it was almost hard and was clean and fresh.
"Would you like a drink, or would you like to join Anne and me, or both?"
"I would like a drink, please."
"Go say hi to Anne while I fix the drinks. Could you take in the snacks, please?"
"Sure, is she dressed?"
"I'm not sure, but she has a hot body so I'm sure she'll be proud to show it off."
She softly knocked on the doorframe as she poked her head in and held up the food. I poured the drinks and put everything away. Since it was just before midnight, I figured they could stay up for another hour or two before they would regret it too much in the morning.
Anne was in the bed with the sheet up to her waist. Tracy was sitting on the side of the bed and they were eating some cheese and fruit. When I entered, Tracy stopped talking. I handed her a glass and then Anne a glass. I was still naked but I didn't care. I work out six days a week, I was twenty years old, and I wasn't ashamed of showing what I had.
Anne looked up at me and said. "Tracy says that Doug is good size, but was wondering what the monster in the kitchen feels like inside my pussy."
"Well, does that mean you girls have decided to share your boy toys?"
"She also said that Doug is asleep, and that doesn't seem fair."
"I have and idea. Why don't I lie down, Anne can put her cunt on my face and Tracy can take the monster for a ride. You can either play with each others' tits, or feed each other grapes, depending how adventurous you are or how old and conservative you've become."
They took the challenge well and I soon heard Tracy saying, "Yeah, rub it right there, harder, harder, rub my clit harder," which got me going, so I grabbed Anne's ass cheeks and pulled her down. I sealed my mouth over her pussy and sucked in on her lips. After a few of those, I attacked her clit and she had her last climax. After she came, she fell off to the side and had tremors. I looked at Tracy, who was bouncing hard on me while she had her nipples in her hands. I grabbed her hips and started to rotate her pelvis as she bottomed out. The new sensation took her over the top and she collapsed on my chest.
I rubbed on her back as I felt her contract around my still hard penis. I gently rocked in and out, as she came down. When she regained control of her body, I sped up and asked if it was OK if I finished?
She nodded but rolled over away from Anne. I got on top and I kept going. She was not very responsive at first, but did build up to another orgasm right after I had my third of the night. It was just before 1 AM. We finished our drinks and I herded them into the shower together. I washed my face in the sink and brushed my teeth again. I heard them giggling so they must have had a lot of fun. They came out and I hopped in. When I got in bed, Anne was alone and Tracy had gone back to Doug's room. I took the t-shirt off Anne, but let her keep her panties. I held her back up against my chest and cupped her breast as I said goodnight.
I don't think either of us moved a muscle all night. When the alarm went off, we were in the same position as when we went to sleep. Anne had to use the restroom so I ordered fresh coffee and some croissants. I got out the orange juice and poured a small glass. As Anne was getting dressed, she asked me to make sure Tracy was up. I went across the way and peeked into the room. Tracy was giving Doug a blowjob and they were both awake. I said, "What a way to wake up. I need to train my toy better. Want to share?"
Doug told me to get lost.
Anne and I both dressed, and were having a cup of joe when they came out. Anne said they would come back and drop off their bags after she showered and did her hair. After they left for the show, I did my workout and ran along the lake. It certainly was a glorious, sunny day. During that time, Doug did his workout and when I returned, we both cleaned up and dressed. We went for a walk and I thought it would be a nice idea to get the ladies a gift. We looked at all kinds of stuff and decided to get them each a silk scarf from Hermes' of Paris. I didn't want to buy jewelry or clothes, so this is something to say they were special.
When they finished at the show, they came back to the room to shower. After they finished that, they said that they were hungry, so they changed into something comfortable and we went to grab some lunch. They wanted a salad after last night's big meal so we all ordered salads. Then we went back to the room and we gave them their gifts. They were very appreciative and after a few whispers, Anne asked, "Doug, is it OK to share? Tracy said you were good and I wanted to see if she was right."
Doug looked at Tracy and when he saw that she was OK with it, he said "Sure."
I took Tracy into the living room and bent her over the couch. I teased her the entire time about just wanting another ride on the monster. I asked, "How much did you have to pay Anne to trade places? I bet she makes you lick her pussy on the way home. Are you a member of the mile high club and if two women are together, does it count?" She was taking it and eventually exploded in orgasm. She collapsed over the couch and just laid there trying to get her breath back. I walked to the counter and picked up my camera. I was taking pictures of architecture earlier while we shopped. I took a picture of Tracy from behind with my spend running down her leg. I walked to the front of the couch and had her look up at me and I snapped a picture. Anne heard Tracy scream in surprise and she came out topless. I guess she was getting dressed and came to investigate the scream. I took a picture of her walking through the door and she just smiled.
Anne said, "Please be careful with those."
"I always am. Can I get a picture of you and Tracy together?"
"Sure, get over here, Tracy, the boys gave us a nice gift. Let's give them one to remember us by as well." I snapped a couple and Anne wouldn't let Tracy put on pants or wipe her legs. After the pictures, they cleaned up and headed for the airport. We each got a serious kiss and we left the room and walked them to the lobby. After we returned to the room, we both took a shower. Doug and I put on shorts and golf shirts with our topsiders. When I said I wanted to take a walk, he decided to come along. He was happy that he came with me on the trip and told me that I had a way of finding women.
"Doug, women are naturally attracted to men that can take care of them. If you're wimpy and not confident, it comes across that way and they are off looking for someone else. On the other hand, some women just aren't looking at all. The remainder is up for grabs. If you're clear about what you want and what they can expect, most women will go along for the adventure. You found the little chippie in New Orleans on your own. Gina and Tandy wanted to try something new, and we gave them that. Tracy and Anne wanted to feel younger again, and we gave them that. The girls at the beach wanted some good-looking, in-shape guys to make them feel so pretty they could attract more good-looking and in-shape guys. It's all about giving them what they want, and getting what you want in return. It's a win-win situation. They will not go home and say those guys tricked us. They'll say those guys took care of us and made us feel special."
Doug said, "I guess you're right again. What do you want to do next?"
It was Thursday afternoon, and we were walking along Lake Michigan and a sailboat was playing in the breeze. I said I wanted to go sailing.
Doug asked, "Are you going to buy a boat?"
"No, let's go find a ride."
We walked down to the marina, and when we came to the parking area, there was a guy around sixty getting some stuff from his car. It was more stuff than he could carry. I asked if he needed some help as I picked up the cooler and nodded to Doug to pick up a rubber tub. The guy stood up, had two bags of groceries, and just said thanks. We followed him down to the dock and he led us through the gate and to his boat. We helped him get his stuff aboard the boat. He then shook my hand and said his name was Frank. I introduced Doug and myself.
"I was hoping to go sailing, but we're from out-of-town. Do you know anyone that may want an inexperienced crew to help them?"
"If you want to go out, you can go with me in the morning. I can ask a few friends if you're trying to go out today. I have some work I need to do before I'll be ready. I'm replacing a sail."
I volunteered Doug and me to help him do his work, and with three of us we finished by 6 PM. He was very appreciative. He invited us up to the yacht club for dinner and we accepted. It turned out that after many years, he'd retired from the Chicago Board of Options Exchange. We talked about option strategies and he was happy that I understood what he was saying. I asked and got permission to call him in the future to run ideas past him. He still traded, but just for himself. We went back to the hotel, he went back to his 52' sloop and since he was a retired man, after all, he told us to show up around 9 AM.
We showed up on time, and we motored out of the marina and then set the sails. We had a great day on the lake. Frank had invited some friends to join us. David and Kristin Allen were neighbors of Frank's and sailed with him often. I took a lot for pictures and we had a good time. The power of the wind was unbelievable, how it could move our 52' boat at such speed. He'd designed the sails and rigging so he could operate them from the helm, so we didn't have to run all over the boat. I would love to say that we were a huge help, but the way he had the sails rigged, Frank could have handled it all by himself. We were back around 4 PM. We stopped at Gino's for pizza and then headed back to the hotel to crash. We decided to head out the next morning but first had to decide where to go. After looking at the atlas, Doug picked Detroit.
Five hours after we left Chicago we saw the skyline of Detroit. We checked into the Hilton and just shared a normal two-queen room. We went on the Ford factory tour. When it came time for dinner, Doug finally tipped his hand.
"Britt, I hear the strip clubs across the river in Canada blow away anything you can find in the states."
I said let's go. When we got to the border, the customs people stopped us and they asked if we had any drugs or guns and why we were coming to Canada. "My buddy says the strip clubs are worth the trip, so we drove up from Florida. I hope they are good."
The customs guy laughed and said they were worth the trip. We stopped and had dinner and then headed over to the million-dollar saloon. The place was two stories of some of the hottest babes I had ever seen. It was totally nude and then some. I reached in and handed Doug $200. I told him that was his limit for the night unless he wanted to reach into his own wallet. I sat back and enjoyed the show. I ordered a Labatt's and a bottle showed up on my table. It was a good thing we changed countries because Michigan was one of the only states that I wasn't old enough to drink in at the time.
Rowan
- 03.02.2023
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