Hindsight 20/20 Book 1 - Cover

Hindsight 20/20 Book 1

Copyright© 2012 by SmokinDriver

Chapter 23

Time Travel Sex Story: Chapter 23 - This is a coming of age story for a man that has gone back 35 years in his life. We can see how he would live differently knowing now what he didn't know the first time. Some codes are listed but not a major theme of the story others could have been listed but were left out for the same reasons. Some chapters have no sex and some contain orgies. As in any long story there is not a constant chapter after chapter pattern. Thanks for reading.

Caution: This Time Travel Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   ft/ft   Teenagers   Consensual   Humor   School   Rags To Riches   DoOver   Time Travel   Oral Sex  

When Shannon came in, I had her drive me to the 24-hour grocery. I bought a couple of coolers, some snacks and beer. I bought ice to cover the beer and we went back to the room to have sex once, before we went to sleep. In the morning, I walked out at about five till nine and there were three cars and nine women in them. Just then, a pick-up truck pulled in with two more girls and then Karen and Michelle. Shannon came out behind me and Amy was with her.

Although there were sixteen people, I was the only guy. I looked at Michelle and she said, "We went out last night and I told one girl and the rest of the night people asked if they could come. You said it was OK."

I said, "Next time I will plan an orgy instead of a float trip if you are going to bring along your pretty friends."

Michelle said, "I'm not sure as many would show up if a guy was going to be there, but we could try it." I got her to smile. It was going to be a good day.

Karen said, "Britt, you are such a man slut."

We all gathered around the steps and I said, "I got two coolers and I think we may need one more depending on how many are drinking and how much they want to drink. I would prefer that the drivers are sober at the end of the trip. I see two cars that will fit five each and Shannon's will fit four. If we put two people plus the tubes in the truck, we should have enough. I was going to stop and get sandwiches. Is roast beef OK with everyone? If not I can buy ham or turkey or whatever you want?"

Michelle said, "Buy half roast beef and half turkey. If there is anyone that has a strong need for one or the other, we will let them pick first. I can pick last and I know Karen will eat either."

"I didn't know she went both ways but that is good to know. I can get more beer, sodas or something else. What does everyone want? I can also get something to go into the sodas if you want to use a cup."

One girl said, "I love Jack and cokes."

I said, "Let's do this. Michelle, can you go down to the ABC liquor and get a bottle of Jack. I'll get two cases of beers and sandwiches. I'll need another cooler and ice so we can all meet at the Albertsons and leave two cars there. I can get cups as well. Do we need two bottles and less beer or is that split ok?"

"Sounds good."

I got out my wallet to give Michelle some money for the whiskey. Everyone else went for their purses. (That just sounds weird). I told them it was my treat and we went in different directions. Some of the girls came in and got the beer since I wasn't old enough. I got everything else and I gave the girl cash for the purchase.

Michelle was in the lot and we packed the sandwiches from the deli and some other snacks along with the drinks and ice. Thankfully, it all fit in the three coolers. We took off up the road and were there by 10. We then had to rent nineteen tubes and tie them down. When the girls asked about the coolers, I said we could put them in an inner tube. They tried but couldn't get the cooler in the hole. I laughed and said you need a guy to get something that big into such a small hole.

I got a chuckle from the crowd but they wanted to see me do something they couldn't so they watched me. I grabbed the first cooler and sat it on top of the inner tube. I then puffed up as if I was getting ready to lift a 500-pound weight. I leaned over and let the air out of the tube. I stretched it around the cooler and then walked over and re-inflated it. The girls started giving me shit about needing a guy. They did the other two and when they were all secure we went up to the launch site. All of the drivers drove to the take out point and Shannon came back with all of the drivers.

We walked into the water and everyone was complaining how cold it was. They were blaming me because of the water temperature.

I said, "Ladies, it is 72 degrees like most springs in the state of Florida. I like to see your hard nipples poking through your lovely bikinis but you will get used to it very quickly. With the sun as hot as it is you will be in the water by choice a number of times today, so quit your bitching. You all have a vote but I think it should be a topless float since there won't be any houses along the way."

A couple girls said "Hey that sounds like fun", but Karen said, "Britt you are such a pig." She then splashed me while I was standing trying to keep my nut sack out of the cold water. I finally just dove in and within a minute had acclimated to the 72 degree water. We all hopped on and floated away. The water was crystal clear and it went from five to ten feet deep most of the way. It is deeper up at the spring but we put in below the spring. We could use our hands to move around the group and float with different people. I put my foot on Shannon's inner tube and said, "This is the life." She grabbed my foot and gave me a foot massage.

That started another round of bash on the mean man. I didn't ask for a foot massage I was just using my foot to stay connected to Shannon. Shannon told them, "Shut up. He isn't making me do anything. The other night I came home from work and was beat. He took me and washed me head to toe. He brushed my hair and then gave me a massage head to toe. That included a 30-minute foot massage and a 30-minute back massage until I fell asleep. He pampered me for over two hours until my muscles felt like mush."

Karen said, "And then he expected you to take care of him right?"

"No, he curled up behind me and held me. He kissed my head until we both fell asleep. In the morning he attacked me and made me cum more times than I could count."

Michelle said, "Been there done that. If he had longer hair you would think he was a lesbian when you look down."

Shannon said, "From experience I know what you are talking about."

We had a good time. As the beers and the mixed drinks disappeared, the girls relaxed more. I took a dip to cool off and then came up under Karen's tube. The hole in the middle is a target that led to her ass. I waited until it was only around five feet deep and I came up, picked her up and flipped her tube. She landed on her head and she was screaming in shock as she went under water. She came up mad at me and started to come after me. I just went under, grabbed her again, pulled her into a hug and kissed her nose. I said, "Thanks for coming today, even if you haven't said one nice thing to me or about me today. I know that you are just playing tough girl in front of your friends." I let her go to swim back to my inner tube and pull myself up and into my tube. Michelle had Karen's tube.

Karen swan over to me and I thought she was going to dump me but she didn't. She said, "I really haven't been nice to you have I? I was just joking but I'm sorry. Thank you for inviting me today and I'm really having fun. I work so hard at school. I can't remember the last time I just relaxed and did nothing."

I grabbed her under her arm and pulled her up onto my lap. I held her in a hug as she leaned against my chest. Michelle paddled over and put her hand on my tube. Amy came up to the other side and Shannon and I had our feet on each other's tube. We floated like that for a while. I'm not sure what she was thinking but I know I struck a nerve with what I said. I just let her know that everything was going to be OK. Things lightened up and eventually I got hot again and used her weight to flip us both over and into the water. She gave me a hug and a kiss before she climbed back into her tube.

We all came together in a big clump to pass out lunch and to eat. More than one person said they were having a fun time and we should do this more often. I did see one girl that took off her top. She reminded me of Courtney Cox in the Bruce Springsteen video. She was somewhat flat chested. Most of the girls were friendly and not the man-hater variety, just the girl-lover variety as I was. Amy was having a good time. She was new to Florida for the MBA program and floating down a river was something she had never even heard of. When I mentioned alligators, she got scared. I told her she could sit on my lap and she almost took me up on it until I leered at her and she decided to take her chances with the gators. I told Shannon to take her top off and she did of course. We floated, relaxed, and enjoyed being with friends for the next couple hours. When we were getting close, some of the girls in the very front called back that we were coming up on the take out point. The topless girls put their puppies away before we made it around the last bend.

We hauled everything and everyone out of the river. We took our trash to the cans and consolidated the cooler stuff. One of the girls took Shannon up to get her car. The rest loaded the tubes into the truck and they drove up to drop off the tubes at the rental place. The rest of us waited for them all to return so we could caravan back to Gainesville. While we were waiting, I told Michelle that I was glad she invited her friends and that I thought they all had a good time. I reminded her that she still needed to plug me into the girls my age that went to her school.

She said, "How am I supposed to do that? I can't just give them a key to your bedroom."

"Can I come by the school and use your darkroom?"

"If you want to, you can, but it will have to be after school and by then everyone is gone."

"My birthday is coming up. I'm sure you have my present all picked out."

"Yep, birthday spankings for you buddy."

"Thanks, do you think I should have a party to start the New Year and have a house warming party for my new apartment?"

"That would be fun. Who would you invite?"

"There are three other units in my apartment building, so my new neighbors, maybe a few guys from the dorm and my harem of beautiful women. That includes you and my girlfriend who is on loan to you."

Just then, one of the other girls walked by and said, "You are Karen's boyfriend? Have you ever slept with her?"

I said, "I don't kiss and tell. You will have to ask her if she has ever woken up in my arms. She is not sleeping with me now, because she is on loan to Michelle. Did you have fun today? It was nice to have a large group. If a gator came after us I had plenty of people to push his way."

"I had a great time. I have lived here for years and never done this before. It was a cheap day of fun and it was very relaxing. Thanks for taking care of the food and drink and renting the tubes as well."

"No problem, you can invite me to one of your parties some time and I can drink your beers and hit on your girlfriends."

"What do you mean?"

"I saw you hitting on Amy and Shannon. I can't blame you."

"Are they your girlfriends?"

"No, I don't have any girlfriends. I once heard a guy refer to himself as a lesbian trapped in a man's body and most of the time, I feel that way. I should fit in very well with your group."

"You did well. We made Tina take off her top to see what you would do. You barely glanced at her and didn't paddle over to drool on her tits."

"I passed the test. I think you should all come to my party, get naked, and see how I do on the harder exams. I'm a straight A student you know. You can ask Karen. I'm studying to be a doctor."

All of the girls had gathered around, some were listening in, and others were talking. An oriental girl asked when the party was.

I said, "I'm not sure. I would like to have it before school starts but they are working on my place. Orientation week is in three weeks. Maybe I should plan it for Friday or Saturday night. I don't want a free for all but I consider all of the girls here my new friends and if they want to come, that is fine with me."

"Where do you live?"

"Over in the student ghetto, on the corner of 3rd Ave and 19th Street, near the stadium."

"Well, let Michelle know and if I can, I'll stop by."

Everyone had returned and we loaded up the cars and headed back to town.

The sun had made everyone a little tired. Amy gave me a hug and thanked me for inviting her. I told her she was there in case I needed a distraction for the gators.

I asked, "I was thinking of tying Shannon to the bed. Do you want to come over and do mean things to her?"

"I never know when you are serious. One minute you say something crazy and you are pulling my leg and the next minute you are saying something crazy and you are serious."

"Well you can always come by and see for yourself."

"I may just do that." She followed me down the hall. Shannon had used the restroom and came in the door with Amy and me sitting in the two chairs.

Shannon said, "That was a fun day."

I said, "Yes it was. I liked you showing off your tits. It made me horny. Do you want to give me a blow job?"

"If you want me to I will."

"Good, take off your clothes and grab a cushion off the couch so you don't hurt your knees."

She started to get undressed. She didn't ask about Amy but looked at her and me to try to figure out what was going on. She was naked when she got a cushion and put it down in front of me and reached for my zipper.

When Shannon was bobbing up and down on my cock, I said, "Shannon, Amy is thinking about exploring her dominant side. I may loan you to her for a couple days to see if she likes it." Shannon slowed down. I told her, "You don't need to say anything. Keep going." I looked to Amy and said, "People know that you can hurt a sub by whipping them or biting them so they tend to be more careful. If you tie them up or even make them get on their knees on a hard floor, they can get hurt as well. Your leg can fall asleep just sitting on it so be careful when you position someone and make sure that they are OK on a regular basis. When someone submits to you, they are giving you responsibility for them and their care. If they complain then you will be upset. They may not complain just so they do not upset you and at the same time hurt themselves."

Amy said, "I never thought of that but it makes sense."

I said, "You can use a safe word. What that means, is, I'm not comfortable with this situation and I want to stop right now. This is not being disrespectful but they are using it to protect themselves."

"Like what?"

"Shannon has the word 'elephant'. If she were opposed to me piercing her nipples and I was about to do that she could say elephant and I would know to stop right now. She may just want to give the illusion that this was against her will. If she said 'please don't, or stop, or I don't want that' then it means nothing except I'm still in control to make the choice for her. If she said 'elephant' then she is taking control back."

Amy was watching Shannon but she was also watching my cock appear and then disappear into her mouth. Shannon was good and if she had her hand around the base, she could almost kiss her hand.

I said, "If I told Shannon to go over and take off your shorts and eat you to an orgasm, she may say she doesn't do girls. If I grabbed her by the hair and dragged her over and pushed her face into your pussy and then told her to eat you while I shoved my hard cock up her ass, I could if I wanted." I ran my fingers through her hair and she was getting me close.

I wanted to give Amy a chance with Shannon to try out her dominant side. I made it a contest for Shannon. I told Shannon that I was close, that I had better come in the next two minutes, and that she had two more minutes after that to get herself off or she would be going home with Amy.

Amy leaned forward to watch Shannon start to work harder.

I said, "Amy count down the clock every fifteen seconds."

"1-45"

Shannon was using her hand on my shaft, one on my balls and her tongue and lips as well.

"1-30"

I was close but started to wonder what the square root of 826 was".

"1-15"

Shannon tried to get me down her throat.

"1 minute"

I looked at Amy and said, "Who are you cheering for, me or Shannon?"

"I want you to win so I can take the slut home with me and have her lick my slit all night long. 30 seconds"

I was close enough. I knew I could hold off but I wanted to make it about Shannon deciding her own fate."

"15 Seconds"

I stood and pulled out before I shot at her face. I said, "Amy, two more minutes on the clock while this slut tries to get herself off."

"1-45"

I guess she had already started the clock. Shannon jumped over and was on her back on the cushion. It wasn't big enough for her whole body so she had her back on the cushion and her pussy in the air. She had one had rubbing hard and the other tweaking her nipples.

"1-30"

I said, "Shannon do you want me to get something to shove up your ass? I will if you want." I was trying to distract her. I wanted Amy to win and have fun with her.

"1-15"

Shannon said, "Noooooo". She was trying to concentrate on the work at hand.

"1 minute"

"45 seconds."

It was an awesome sight to watch. I had seen women masturbate before but never with such intensity and never with so much at stake.

"30 seconds"

"15 Seconds"

Shannon let out a groan. It was not an orgasm but frustration.

"10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 0"

I said, "Keep going to see how long she gets to keep you. You had better hurry. Benji will be pissed if he has to wait three weeks after he gets back."

She kept going and finished in about twenty seconds.

She looked dejected. I grabbed a towel and wiped my cum off of her face. I then went over to a box of mine and got out a leash that I had from Monica. I slipped it over Shannon's head and handed the leash to Amy.

I said, "Two things Amy. Number one, her safe word is elephant. If she says that, you will stop and bring her to me do you understand?"

"Yes"

"Number two, I want to watch Shannon eat you the first time."

"That is fair." She stood and dropped her shorts. She was one of a couple girls I had seen this time through that had her pussy shaved clean.

"I like the hair style, Amy. I have Shannon keep the labia clean but she just keeps her mound trimmed. If you want her to shave it off you can."

Amy tugged on the leash and Shannon walked to her. I kicked the cushion over to her and Amy sat back down and put her legs up on each arm of the chair. She scooted forward and Shannon started to kiss and lick.

I said, "Shannon, you have to remember that I could have held out but I wanted to give you a chance to win. I left the results of the victory or defeat for you to decide. You were being lazy earlier. You know I like you to play with yourself when you suck my cock. You didn't because Amy was here. If you had done what you normally do, you would have been much closer when I came. If you had worked harder on me earlier, it wouldn't have been so close for me either. Do you understand that you have brought this on yourself? That I did not do this to you, but you did?"

She actually stopped. I was expecting her to nod her head and continue, but she stopped. She looked at me and said, "I'm sorry, I know it was my doing that got me here. I'll let Amy explore being a dominant on me." She turned back and started to suck on Amy's clit as her fingers worked inside of Amy.

It took just two minutes to get Amy into her first orgasm.

I said, "You don't have to take her to your room but you have completed your part of the agreement."

Amy said, "Thanks, I would feel more comfortable up in my room if that is OK?" I shrugged and nodded.

Amy took the leash. Shannon stood and put the cushion back. Amy put on her shorts. I was wondering if she would make her stay on the leash, if she would let her put on clothes or what.

Amy said, "Do you have a robe?"

"Yes" Shannon replied.

"Put it on and carry your clothes." She was going straight for the humiliation approach. However, would she leave the leash on?

"Shannon, I'm going to let you off the leash but you will follow two steps behind me. If you get too close or too far away I'll put it right back on do you understand?"

"Yes ma'am"

"OK, let's go."

I watched as they walked down the hall to the stairs. To test her, Amy stopped completely twice and sped up once. Shannon stayed two steps behind her. I was beat but hungry. Between semesters, the cafeterias close down so I grabbed my bike, rode over, and got a slice of pizza. It was awesome. I ordered a pie to go and then rode back carrying the pizza in one hand. I walked up to Amy's and knocked. It took a minute but she answered with just barely a crack to look out. She saw who it was and smiled. I said, "I didn't want either of you to starve. I opened the box, grabbed two slices, and turned one on top of the other so the crust side was out on the top and bottom. I closed the box and handed her the other six slices. She thanked me and opened the door. She had to let the towel drop. She had nice tits and again the shaved mound looked hot. I saw Shannon on the bed with a dildo sticking out of her cunt while she was on all fours. I turned and left with my pizza.


Monday.

I had been slacking off, so I did a little extra of everything in my workout. I cleaned up and went over to my apartment. The progress was amazing. They had completed the painting, the floors were close to completion, the counter tops were going in today, the tile was set and they had scheduled the grout for today, and the painter was outside painting baseboards so they could install them later in the week. I walked out back, the pavers were half done but they had completed all the removal of sod, and leveling and they had installed the sand base. If they delivered the furniture quickly, I would be able to move in at the end of the week.

I told Steve that things looked good and he said the guys were doing well and that they should complete the pavers by tonight. I took that as a hint that, by tomorrow, I should be prepared to make payment for the labor. I headed over to meet with my counselor. We had laid out my classes last year but they still need to sign off every year. I went over, bought all of the books for the semester and took them back to the dorm. It was only 2 pm and I had finished what I had planned to finish in a week. I needed to get a hobby.

I stopped by Amy's room to check on Shannon. I was a little worried. Amy answered the door and they were just getting ready for lunch. They looked like new best friends instead of master and slave. They both had clothes on and seemed happy. They invited me to lunch and we walked to a diner about ten blocks away.

I asked, "Did you girls have fun last night?"

Amy said, "Yes and this morning too. Karen and Michelle stopped by because they didn't want me sitting home alone and they were both surprised at what they found. Karen said to tell you that you are a pig."

"Did you learn anything about what you are looking for in a relationship?"

"Yes I did. I wanted to be so in charge and humiliate her so much. I wanted to walk her down the hall naked and show everyone my bitch. I soon discovered that I only got satisfaction when she was being satisfied, like a parent that has the ability to make their kids do anything including eat their vegetables. When the kid is sitting at the table for an hour after dinner trying to choke down six brussel sprouts, it isn't fun for the kid or rewarding for the parent."

"Shannon put herself in my hands and when the new puppy fun wore off I still had to feed it and clean up after it. I think I had a fantasy about doing some of the things but not the full-time responsibilities that went with it."

I said, "What about you Shannon? Did you learn anything?"

"Yes, I was disappointed that you gave me to Amy even though I lost the contest. I was also excited about what was in the unknown. I have been with Benji for eleven of my twenty-four years and I just didn't know what was on the other side of the door. I'm only twenty-four and have had more sex than most people twice my age. If sex were eating ice cream, I would have had a gallon a day for the last eight years. It isn't the quantity but I have only had vanilla. After you traded your slave for me last year, I have found out that even Baskin Robbins had thirty other flavors. Some of them are pretty good."

I raised my eyebrow and said, "And?"

Shannon said, "You alone are Baskin Robbins, but there are other ice cream parlors as well."

"That is an interesting concept. What is the outcome of your new discovery?" I asked.

"I need to have a long talk with Benji. He is always looking at other women. He is very sexual and we fuck like bunnies but bunnies don't use clothespins on their nipples while they shove a cucumber up their cunt. They just fuck like bunnies. I think we need to either try new things together or take a break to get some variety. Monica was much different from me and I'm sure that my friend back home is teaching him some new tricks. We have become creatures of habit."

I said, "Yes people are that way. In college there are almost no classes with assigned seating but after the third time the class meets, most people will sit in the same seat or at least the same area each class."

"I know and I want to check out the other side of the room. I want to sit in the front row and the back row and I have had a little taste of that."

"Did being with a woman freak you out? I know that Monica ate you once but you were on the giving end yesterday."

"It did a little at first but I think the fact that she shaved gave it a different feel. That helped me get past the first couple of minutes and then I just wanted to explore so I wasn't worried about the rest of the woman but just seeing how I could make her pussy respond."

I sat back and said, "I'm proud of both of you for stepping out of the box and exploring new things and being honest with yourselves about how you felt about it. I think we should all go back and have a mini orgy to celebrate."

I was giving one of my smart ass remarks to get a "Britt you are a pig" reply but Shannon said, "Sounds good to me."

Amy replied, "OK."

As I was telling Cindy on the cruise, it never hurts to ask. We left the diner and walked back to the dorm. I said, "I stopped by the apartment today and the workmen are flying through the project. I wish it was done now so we could just go there."

"That would be nice because the furniture in the dorms just doesn't cut it for a comfortable orgy. At least in your room there is a queen-sized mattress. In the double rooms the mattresses are singles." Shannon commented.

I did get to have sex with Amy. I could tell she was still a little concerned about the age difference, but once I had my dick seated in her, and started to stroke in and out with Shannon working on her tits, she just closed her eyes and obtained great pleasure from the ride. She did have some pointy nipples. Most of the women I have been with have flat nipples on top like a pencil eraser. Monica's were rounded like a bullet but Amy's almost came to a point like the sharp end of the pencil after it had been used for a week."

We played for a few hours. We all were in a mood to please the other two, so we took turns suffering through letting the other two take care of us. It was not hurried or uncomfortable. Shannon did take some orders from both Amy and me and one time I had her eat Amy while I fucked her from behind. I was trying to use condoms more but I liked bareback and knew most of the girl's history before we started. I was more worried about pregnancy than STD s. The girls said they were safe to I let it slide. I would be OK to support a child. I just didn't want the responsibility of fatherhood and the other things associated with having a child. I let the women lead the decisions.

We split up for showers and then had a hamburger at McDonalds. I try not to eat there too often but we were being lazy. I'm happy that I did the extra workout today. Without anything being said, Shannon came back to be with me. She needed a break from almost twenty-four hours of sex so we just talked and played backgammon. We just held each other when we went to bed,

The rest of the week, I took my bike and rode around. I kept making further trips out into different parts of town. I was exploring and letting my friends take care of their own stuff. I did find two stores where I made purchases. One was a wood shop. The guy was in his 70s and he had all kinds of different projects that he had built. I told him what I was looking for and he said, "Yup I can make dat fer ya."

His name was Frank Walker and he asked about the type of wood. When I explained the Adirondack chairs would be outside on the patio he suggested cedar since it would hold up better in the weather. He also suggested a small table in between. I said, "I want the arms to be wide enough to hold a drink or a book if I wanted to set something down."

Frank said, "Yup, but where are ya gunna put the cooler with the rest of yer beers?"

I said, "I think I'll need that table Frank."

"Yup, I can have em for ya next week."

I got his number and told him I would call and arrange him to deliver them when I moved in.

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