Hindsight 20/20 Book 1
Chapter 24

Copyright© 2012 by SmokinDriver

Time Travel Sex Story: Chapter 24 - 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  

Over the next few days, the rest of the tenants trickled in. Some knew about the renovations because they were there in the summer but most were surprised and happy to see the changes. I actually knew one of the guys upstairs. John Peterson went to Winter Park High School. He was two years older but we graduated together and he was now a sophomore here at Florida. We had not been good friends but we knew each other from common friends. His roommate, Mark, was from Jupiter, Florida, on the east coast.

April made it in on Thursday and took a cab from the airport. It was good to see her and she seemed happy to see me too. Her roommates, Fran and Tori, seemed nice enough. Stella also had two roommates, Tiffany and Daphne. It seemed like a good group in the building, made up of just sophomores and juniors, no seniors.

To kick things off I decided to have a party. I didn't want it to be a block party so I just invited my neighbors. That is three guys and six girls (good odds so far). I invited Reggie and his sister Dani, Brett (Reggie's roommate) Benji and Shannon, Amy, Cathy, Karen, Michelle and any of the girls from the float expedition that they wanted to bring. I thought about inviting more guys but decided that I didn't have any closer men friends, so I let it go.

I ended up inviting thirty to forty people with only a few guys. I had some concerns that the lesbians might make some of the other girls feel uncomfortable. I decided that they were all friends so I couldn't be responsible for other people's feelings. I put out the word for a Saturday night party to kick off around seven. I had April help me get everything together. I purchased a full bar set up, and even if we don't drink it now, we can have it for later. We also had a big cooler full of beer and another with sodas. In addition to wine, April picked up some snack food.

Some people couldn't make it and most knew some of the other people so groups formed and people intermingled. Reggie introduced his sister around and I did the same for Cathy. She knew Stella and hit it off with John. I think she left with him but I wasn't sure. I hope she is more careful than the first night of the cruise. There was music playing so many people danced since the whole place had wood floors. Some of the girls from the float were kissing and of course dancing but no one made a big deal about it. I even danced with the little pixie that took her top off and a couple others. I also danced with most of my neighbors. Everyone seemed to have fun and people started to leave around midnight so around one there were just a handful of people left.

Reggie, Karen, Michelle, Dani and April were hanging out in the living room. When I went by to invite Reggie over, I had gotten a big bag of weed from him. He gave it to me at no charge. I asked if anyone wanted to smoke a bit, and everyone except Dani said yes. Dani said we should go ahead as she said, "If I weren't here on an athletic scholarship I would be first in line."

While they passed the bong around, I got some extra cold water from the beer cooler. After we all were feeling a great buzz, Reggie told us the story of when he had to go to Vegas. His sister didn't know anything about it so she was surprised. Only April and I knew the whole story or so we thought.

Reggie said, "Britt and I were talking about betting on something because he almost never loses. I needed some cash and we were just bullshitting about the possibilities. I told Britt if he placed a bet to place one for me. He isn't old enough to pick his own nose so he took April with him to Vegas. While they were there, he not only bet on the Derby but he took April to the craps table where she won."

April said, "I probably would have lost if Britt hadn't made me quit while I was ahead."

Reggie said, "Anyway. They won the Derby bet and placed a bet on which horse he thought would be the winner of the Triple Crown. That is a bet on three races where the same horse has to win all three races or you lose the bet. By the time they got back from Vegas, my horse had already won the first race. The horse won the next two and I had won my Triple-Crown bet. It paid 200 to 1. Britt had put $100 down for me so I won $20,000. I had to fly to Vegas to claim my winnings."

After the talk about the $20,000, they asked why I didn't buy everyone a ticket.

He said, "I flew out and was going to fly back the next day. I went straight to the casino and was very nervous about winning and how hard a time I was going to have claiming my money. I had to fill out a form for the IRS because of the size of the winnings and then they asked if I wanted a check or cash? I told them cash and I walked out with a bag of hundreds."

"I checked into the hotel and paid cash. I had been in fear, so much so that I was afraid to take a check because I thought that they would stop payment. I was now afraid to have the cash, because with all that money, I was placing myself in position for a robber to steal it. Here I am, a full-grown man sitting in my room with a bag of money in my lap, afraid to go out in a city that screams 'come out and spend your money'. I sat there for an hour and was terrified to let it go." All of us were stoned and laughing at Reggie.

He continued, "I finally got hold of myself and hid the bag under the sink in the bathroom. I had $1,000 that I was willing to blow. I asked myself, what would Britt do? I have taken statistics and I knew either I could spend all night watching my money walk away a chip at a time or I could take a risk. I went to the roulette table and played the end of the table. I took the middle row as it covers about a third of the numbers on the table, not including the zeros. It pays 2 to 1 odds. I played all of the $1,000 on the middle row and literally held my breath and didn't realize what I was doing. That ball seemed like it went around 100 times before it finally dropped. I was about to pass out when it hit the tray and landed. He placed the marker on the number and started to clear off all of the losers. I had won. The guy put two stacks of 10 $100 chips next to my one stack so I now had $3,000 dollars in chips in front of me. I cashed out $1,500 and put the dollars in my pocket. I kept $1,500 out so I could keep playing. I was going to walk away when I ran out of chips so I would be up $500 guaranteed.

I went over to the craps table and came up next to a lovely lady who was very hot looking. I asked her if she could help me understand the game. She was playing $10 chips. I got $400 in chips and started copying her. After a while I learned that the table gets hot and then cold. I guess I must have been good luck and the table got smokin' hot. The pit bosses were on the phone to the eyes in the sky it was so hot. We were all getting excited and this chick is calling me her good luck charm. She changed to start betting $20 a pop and I moved up to $50 a shot. We went around the table in shooters twice and everyone was doing well. Finally, the guy across the table threw the dice and one went off the table. Then he crapped out. The next guy shot craps the first roll. I picked up all my chips, and so did the hottie named Simone.

I asked Simone to get a drink with me and we went over to the bar. I had followed her lead and got larger $1,000 chips. When we sat down in the bar, we ordered some vodka tonics and I counted my chips. I had $5,350 after I tipped the dealer $200. Simone had close to $2,500. I also had the $500 I had cashed out for a profit of $5,850. I had $19,000 back in the room. I had collected almost $26,000, but I had to pay taxes on the $20,000, so after taxes I have $18,000. When we finished our drinks, we both wanted dinner so we took a cab down the road to a steak house. We had a great meal and on the way back we got a cab and she said that we should go to a strip club. I said, "Sure."

Simone is a sales rep for a computer manufacturer. She sells cash registers to grocery store chains. She was in town for a convention and had stayed an extra day before she was to fly back to her home in Atlanta. We went to this club and had a blast. We were both getting lap dances. I said we should go to a club and find a girl that we can take home with us and have a three-way. I would have never thought of that but it was what Britt would do.

She said that would be fun. She said, "If we strike out we can still do each other."

We went to the club at the hotel and there were tons of hotties. We started to dance and she saw one girl she liked. She stayed out and danced. I went and asked the other girl to dance. She said sure. I took her out on the floor and we danced for a while. I moved her over to where Simone was dancing. I introduced them and then kind of let her know that WE were interested in her, but she immediately lost interest in us. We decided to just dance alone for a while.

We were out there dancing and the next thing you know, she pushed me back into the middle of a circle of girls drunk off their butts who were attending a bachelorette party. I just kept dancing and the girls went a little wild. Simone talked to the bride-to-be about me becoming the stripper for their party. The bride told her that she had promised her fiancé she wouldn't hire a stripper. Simone was now acting as my pimp and loaning me out to the girls as a male dancer. I really didn't know why. They wanted to go up to the room and I was not sure where we were going. I didn't want to go to my room because the money was there. The girls were staying at a different hotel and Simone was not offering her place.

I was going to get another room but then if anyone went to my room I wouldn't be there. Still, I got another room. We all went up and the girls sat down and turned on the radio by the bed. I started to dance. The girls were cheering. I lost my shirt and then my shoes and socks. That was somewhat awkward. I started on my pants and the chanting started. I did the slow tease that I had learned at the strip club earlier. When I got down to my underwear, my cock was hard as a rock and it was trying to make its way out of my shorts.

Out of nowhere, Simone took off her blouse and bra and dropped to her knees. She took down my shorts and took my cock in her mouth. She started to jack me off and suck me off to the beat of the music. The girls were all cheering and a couple got up and came over to touch me and rub me. It was Simone, seven more girls and I. Simone sat back and another girl got down and took her place. The girls all started to get naked. The third one said, "Please fuck me." I had one condom in my wallet and eight girls with me. I told them and one girl said, I will go down and get more. I gave her some money since I had my wallet open and she went down to get a box.

They pushed me down and it was tits and ass wherever you looked. I had women on my face, on my cock and in my hands. The big kicker was when I looked over and saw Simone with her skirt up and her cock buried in the bride. She was wearing a condom, I was glad to see. She or he had sucked my cock and we had kissed earlier. The bride was having a good time from the looks of it. I did have sex with another girl before we ended the get-together. Simone wanted to come back to my room to spend the night but I was very uncomfortable with what she or he wanted. I also didn't want to have her in my room with the money or leave the money alone while we stayed here. I told her that this was beyond my normal and I didn't want to be rude but I thought we should go our separate ways. She understood and I did let her give me a hug before I went back to my room alone. I barely slept and was on the first flight out in the morning. I was at the bank when it next opened to deposit the cash. I came back here and crashed. I slept for twelve hours straight."

I said, "That was some story. I would have picked the money up for you if you had asked."

He said, "You suck."

I said, "But not as good as Simone."

Karen asked, "How much did you bet, Britt?"

I said, "I am not old enough to bet. It was April."

April said, "We bet five grand."

I looked down. I did not want this out there with my friends.

They were all doing math in their heads trying to see if the zeros were right. Was it $100,000, $1,000,000 or $10,000,000? When Michelle was sure of herself she said, "You won a million dollars."

I nodded. "Yeah, I had to pay taxes and some other obligations but the rest went into my trust and is invested for the future."

Dani saw that I was uncomfortable and said, "I really liked your pictures. Everyone was commenting on them. I thought you bought them until I saw you had signed them."

Michelle said, "I taught him all he knows. He is a very good photographer. I heard many comments as well. I may have heard some volunteers if you need some models."

Reggie said, "A million bucks. Man, that's so cool. Have you ever lost a sports bet?"

I said, "Sure, I lost a couple with April when we were out there." When you box a race bet that means you are going to lose some of them. If you box a tri-fecta with three horses, you are placing six bets. At least five will lose, but if the sixth one wins, it covers more than the cost of the five losers.

Dani said, "Reggie, I am ready to go home. Will you walk me home?"

Karen and Michelle left as well. April and I were the only people left. I did clean up a couple things but the rest could keep until the morning. Since I had not had any time at all with her, I asked April to stay with me. Since there were no other people around and we were not busy right then, she said she would stay the night. However, since she lived just upstairs, she was going to go upstairs first, change and take off her makeup. She was also going to leave a note for her roommates.

She was back in about twenty minutes. She didn't have on pajamas but did have on some shorts and a t-shirt. When we got in bed, I gave her a kiss, then lay back, and pulled her head onto my chest as I stroked her arm and back. At the same time, she had her hand on my stomach. I said," I have missed talking to you. You and Angus seemed to be getting along well when I left. How did that work out?"

I felt a tear on my chest but just reassured her with my touch. She said, "I think he is the one. He is kind and smart. He is his own person, meaning he doesn't cater to his parents or mine. I think he is genuine and not playing games with me."

"He seemed to care for you deeply. He drove me to the airport to ask for my permission to pursue you. He wanted everything upfront and on the table. I like a person who deals with problems or potential problems head on."

"He said that he spoke with you and that I was free to make my own decisions about him. I felt like we broke up and I felt hurt that you didn't stand up for me, that you were giving me away."

"April, I understand that. If you were my girlfriend I would have told him in no way could he even look at you. I have told you what my plans are. I am denying myself a relationship with you and with some other very nice women as well. To be truthful, this is simply a selfish move on my part. One day I will be married to my job. Would you like to spend ten years seeing me once or twice a month? I would not be able to survive that and you would be miserable. I have enough money that we could move to Hawaii and retire right now. Is that what you want out of your life? When you are sixty and some one asks you to tell them about your life you can say 'I sat on the beach for forty years when I wasn't traveling or fucking'?"

She said, "No, I want to be an engineer and I want to be in a position where I can solve problems. I was just hoping I could do that with you. The reality is that I can be an engineer in Hawaii."

"I know you could, but I want to retire at age forty. Not because I have finally got enough money, but because I have achieved my goals for my life in business."

She asked, "What are your goals for business?"

I said, "I want to build a business. I want to hire the best people to run it and I want to have families that own homes and cars, families that have children and take vacations and have the means to do so because they work for my company."

She said, "I have never thought about that. The way you phrased it was very inspirational. You didn't mention a product or service but what the result of selling that product or service would do for the people that worked for you. Daddy has a business and has 100 different families that live well as a result of him providing jobs."

I replied, "Even more people, if you look at the ones that clean the office, deliver packages, cater lunches, assist when they travel, provide insurance and other services they use everyday. Remember the "trickle down effect."

"Thank you, Britt. I am more proud of my dad because of this talk."

I said, "You mean the talk where you get off topic so you don't have to talk about what happened with Angus?"

"That would be the one. Angus and I had a long talk before we went back to school. We want to keep dating and he could be the one but we both know that long distance relationships will not work. I don't want to miss all the fun at college just to sit at home. I don't want to be afraid of meeting a guy in one of my classes that I fall head over heels for, and I think a commitment to Angus about that would destroy that chance. We all know that the women in Boston are sluts so he will have women throwing themselves at him daily."

"Out of the mouth of a true Yankee fan. So you broke up?"

"Yes and no. We will try to call each other once a week at least. He said that we could see other people. He would rather that neither of us get into a heavy relationship and just go out with people for the social aspect. When I described your motto on dating, he said, "That is what I am talking about but you don't have to get laid by eight different people every week. If you do, please don't tell me about it."

I said, "So you told him I was a slut."

"He was very interested in your story. I don't know it all but when I finished he had all kinds of questions. I told him I didn't know."

"So my job is to give you enough sex so that Angus doesn't have to worry about you picking up strays. I also can love you but can't let you fall in love with me so that you will be ready for Angus when he is ready to swing his dick your way full time."

"That is kind of crude," she said. "But I think you have the general concept. We did sleep together a couple of times near the end of the summer. I may have to send him to your sex camp next summer so you can teach him a few things."

I said, "I can loan you my chains and you can train the pup yourself. April, when I turn forty, if you are divorced, I will marry you or at least take you into my harem and support you until you are too ugly and I have to trade you in on a newer model."

"Thanks. With that attitude you could fit right in up in Newport."

"So, just making sure, you and Angus both agreed that it is OK for me to rape your body whenever I feel like it and you will be my sex slave for the next three years to keep you from straying off with another master."

"Rape is such a harsh word. How about sexually use my body when it is convenient for both of us. We will be as you said, friends with benefits for the next three years to keep down my sexual tension so that I don't stray off and take another substitute."

I replied, "Substitute is such a harsh word. Why don't you suck my dick while I think of a better one?"

She was right there so she bit my nipple. Then as I complained about the pain, she went down and took my cock in her mouth. We took care of each other orally and it was late so I fucked her one time. She must have enjoyed it because she almost broke my eardrum.

When we were done, I held her naked body against mine. I said, "I may need to get you a gag or wear earplugs next time."

"That is what I missed when I was with Angus. He makes sure I get off but he doesn't get me off when we are fucking."

"I really don't want to talk about you and Angus fucking unless you have pictures. It may be size or technique. Maybe he doesn't last long enough to get you home or maybe he doesn't get you ready enough on the front end. You should try different things and see how they work. Take a couple weeks and figure out what you like and don't like. Maybe he needs to shove a vibrator up your ass as he is doing you."

"That is a good idea except for the vibrator up the ass. That is, unless it is a last resort."

I kissed her and we both went to sleep. I woke up late in the morning. My new bed was great and the naked woman by my side felt good too. She eventually woke up so I got up and made coffee. I cut up some fruit and berries then added whipped cream on the side. When she came out and I handed her the coffee, I walked into the bedroom with the fruit. She followed me and we sat in my new, very relaxing chairs. The armrests were wide enough to hold the coffee and the fruit, but there was a table between us to handle the used dishes. The pool looked nice, so much so that I was looking forward to taking a dip. We had a nice talk and we were enjoying our time together. Stella came out of her door wearing her suit and heading to the pool.

I didn't want to freak her out if she saw us so I called out, "Good morning, Stella."

She saw us and walked over. "Thanks for having us over last night. It was nice, just like a little block party."

"Thanks for coming over. It was nice to meet the neighbors."

She asked, "How do you know the others?"

"Well some were from the dorm I lived in last year. One was a teacher from my first semester and the others were some girls I met."

"I am not trying to judge but a few of them looked like they may not be interested in you. Where did you meet them?"

"If I told you that they used my cock as a model for the most popular style of dildo on the market today, and I met them at a box signing at an adult toy store, would you believe me?"

"I would say definitely not. But that is the most absurd story and it came out so fast I am not sure."

April jumped in. "You could ask him to see his cock and then compare it to the one in your night stand."

 
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