Orgasm Diary September 2020
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Hindsight 20/20 Book 1Chapter 17 free porn video
Friday after class, April drove me down to get my driver's license. She thought it was funny. She said, "I feel like a mother, nervous for her son. Hey, have you ever even driven a car? I know you have one but I have never seen you drive or practice driving. Can you parallel park or do a three point turn?"
I said, "Take it easy, Mom; I have been watching people drive for years. It looks pretty easy. Besides, I know the rules of the road. I read the driver's handbook."
They eventually called me to take my test. The examiner walked out to my car with me. She was young, like mid-30's. No grey hairs yet. I said, "Good afternoon. My friends call me Britt."
"Hello Britt, you can call me Mrs. Fleming."
"Ok, I am parked over here."
She told me to get into the car and turn on the lights, then to hit the brakes. She checked the tags before she got in the car. I had my seatbelt on and waited for her to get hers on as well.
She said, "I want you to drive down to the cones that are set up and parallel park. When we finish there, you will do a three-point turn and then I will take you out on the roads around here. You will follow my instructions. Do you understand?"
"Yes, Mrs. Fleming. Are you ready?"
"Yes, you may start."
It was a standard transmission so I dropped it into first gear and we started. I lived in a couple of cities with downtown street parking, so the parallel parking was easy. The three-point turn was simple. When we went out on the road, I was comfortable so she tried to fluster me. She gave me late instructions to see how I would react. I was doing what she asked. She finally got me on stopping too far in front of a stop sign due to an overgrown hedgerow that I couldn't see past without moving forward. With that she could ding me on something, and she had me drive back to the office. I got my picture taken and we were on our way.
I said, "Mom, thanks for taking me to get my license. Do you want to get some dinner, to celebrate?"
"I need to study but we can get together after class tomorrow."
"No problem, thanks again for helping me out."
We talked later and I learned that April had been with one boy and she regretted it. She wanted to wait for her husband but on one of her dates, she overreacted sexually, and he took advantage of her. He was young and not very good so she did not enjoy it and she felt bad about not keeping her promise to herself. We were good friends and played tennis or golf most Saturdays and saw each other in class during the week. On Sundays, we would go to breakfast. We would go back to my room where we would perform oral sex on each other. She would read a book while I read the paper. We would then have lunch and go to the grocery store. I was free to see other girls but she didn't want to hear about them. We would sometimes do some photography together and she liked the developing process better than learning the picture taking side. She was getting very good at it.
Dawn hinted at getting together but I was over the drama and was happy to fall into a routine for the rest of the year. I invited April home for Thanksgiving but she flew home for both Thanksgiving and Christmas. I went home for Thanksgiving and went to Atlanta for Christmas. Mom flew up and we had a good time. Bill had asked her to marry him and she had accepted. They would be married over the summer.
Spring Break came along in February. We could drive to the closest beach in about two hours but we couldn't see what would be the fun in doing that. I asked April about her plans and she said she was going home.
"April, are you planning to go to New York for a vacation in February? Let's go somewhere fun. The Bahamas, Mexico, Daytona Beach or if you want the cold let's go skiing out west."
"My parents wouldn't pay for me do go to any of those places."
"I need a chaperone and will pay your way to look after me. I would love to do some diving in the Cayman Islands."
"I think that would be fun to go to the beach but could we stay in the country? I don't have my passport and if things went crazy, my parents would flip out."
"Let's just drive down to Sarasota and lay on the white sand. We can be there in three or four hours and you can tell your folks that a friend invited you home for Spring Break."
"OK. Let's do it."
We had a great time swimming and lying on the beach. We rented a sailboat one day and April showed me that she had a lot of experience on the water. The Hobe Cat we rented was like a knife cutting through the water and although I thought we would flip it a couple times, she showed that she was in complete control. We had so much fun we did it again the next day. The wind was not as strong but we still had fun. April told me her family was big into sailing and she has been on boats every summer since before she could walk. She was tired of the intensity of the racing and competition back in Rhode Island but was having fun with the smaller boat and no expectations.
She did break down and ask me if I would make love to her one night. She wanted to see what it was like with me instead of Mr. Clumsy. I told her I would the next night if she still wanted me to and she thanked me for looking out for her emotions. She still wanted to the next day so I went and got a box of rubbers. After the first time she was in heaven and we finished the box of six before the night was over. She was sore the next day but was happy.
I asked her why she had changed her mind about having intercourse with me.
She said, "I was worried that when I got married, my husband would make me feel like the jerk, Freddie, the first guy I had sex with. I was afraid that I would hate to have sex with my husband or any man. You have shown me what a wonderful feeling I can have with a man. Thank you. I still don't want to have sex all of the time but maybe on special occasions you can get some rubbers and we can do it again."
I was feeling the blue balls coming on already after that comment but we were not exclusive. I had run into Carrie and she asked if it was OK to call me if she had an itch that needed scratching. I had Monica stopping by every week or two and if I asked really nice, Karen would let me have a sympathy fuck from Michelle. I was having oral sex with April, just not as often as I liked. I shouldn't complain. I was lazy and could have gone after a permanent relationship any time I wanted.
Shortly after our spring break trip in February, I told April that I needed a chaperone for a trip to Vegas. I booked a suite at the Tropicana and we flew right out of Gainesville but had to connect in Atlanta. We checked in and her eyes were sparkling, with all of the bells and whistles of the casino. We went up to the suite and I had to use the rest room. We had each brought a small suitcase, I had my backpack, and she had her purse. When I came out, she was sitting on the bed counting money. Britt, you have $30,000 here. What are you planning to do? She was just being nice, not nosey. She had already unpacked both suitcases and was going to help with the backpack when she found the stacks of $100 bills. Fifty in a pack and there were six packs for a total of $30,000.
"I am not old enough to bet so I brought along my good luck charm to help me out. Why don't you come over here and let me rub on you to get that luck working?"
"You can rub on me but if you can't gamble how will I know what to do. I know how to play black jack but don't understand craps or the other games."
"We are here for a horse race. We are going to place a series of bets. You will place the bets and then give me the tickets. I will pay you 10% of the winnings for being my helper." I sat down at the table and wrote down the agreement twice and signed both copies and then dropped the pen and moved so she could sign as well. She thought it was over the top but when you win $1,000,000, sometimes people change.
I picked up the first $5,000 bundle and handed it to her. "This is to bet on Affirmed to win the Triple Crown. The odds should be around 200 to 1." I handed her the next two bundles. "This is for Affirmed to win the Derby the odds will be around 2 to 1 if I had to guess." I handed her the fourth bundle. From this bundle, I want you to bet a $10 boxed Trifecta on the following horses Affirmed, Alydar, Sensitive Prince and Believe It. Those are the top four horses in the race and if they finish it will be around 300 to 1 but only one $10 bet will win if at all, so we would get around $3,000 on a $240 total wager. The rest of the bundle is for you to have fun. I will try to get on the floor since you only have to be eighteen, but I will cheer for you or console you if you lose."
"I have $5,000 for shopping and the other $5,000 just in case. Are you ready or do you want me to rub you some more?"
"I saw the box of rubbers, do you know something I don't?"
"I know that a boy scout is always prepared and I don't know where the closest drug store is in Vegas."
I got a kiss and a grab before we headed out the door. We went down to the Sports Book and the place was dead. She had her piece of paper that I had written everything down. She had $20,000 with her and the guy took the bets without a question and said that will be $15,240. She handed him $15,300 and she got two tickets back, one for the Derby bets and one for the Triple Crown. She handed them both to me and I told her to hold onto the Derby ticket. I told her to put another $100 on Affirmed to win the Triple Crown for Reggie. She did and got another ticket. The Triple Crown would take a month to finish. We went to a very nice restaurant and then up to the room for some oral sex and then to bed. Vegas is three time zones behind us, so when we went to bed at 11:30 it was like 2:30 am at home.
I did bring my workout clothes, and April watched me do the first part before I tied my shoes and headed out the door. It was still early, but the East coast tourists were already feeding the slots as I walked through the casino. I ran for about thirty minutes and then turned around and ran back. While April painted her toenails, I changed into my bathing suit and I went for a swim.
She wanted to shop so she took the remainder of the $5,000 bundle, I handed her another $5,000 and she held her purse tight. We stopped for breakfast and then went to the shops. They had some more modern and trendy clothes so we both added to our wardrobe. I was tired of the same department store crap so it was nice to have better material and some funkier designs than I could pick up in Burdines. April got a couple of new dresses and some shoes. I also made her get some new lingerie and a bigger suitcase to get it all home. We went to a nice place and had some lunch. By then it was around 2 PM and as I said, we were three hours behind so we wandered to the Tropicana Sports Book to watch the race on the big screen. It was crowded for the race but we found two seats and settled in. She ordered a martini and I got a coke. I explained to April why I had her place all of the bets and what we wanted as the desired outcome so we could make some money.
Well, as you probably guessed, I had it down. I remember watching the races with my dad the first time through and everything fell into place. April surprised me by standing and screaming at the screen for the whole race. By the time it was over, everyone knew that she was a winner. When she collected on both bets, she had about $12,500 more than what she started with. She also had the rest of the $5,000 bundle from shopping. She wanted to get back to the room since she wasn't comfortable with all the cash in her purse. When we got to the room, she let out a big sigh and then jumped me. She had her legs around my waist and her arms around my neck. She was a ball of energy.
"Get out the rubbers; I want to fuck you for making me feel like this."
She had three martinis while we were in the Sports Book so I wasn't sure what to do. I asked, "Are you sure, because you have been drinking and I don't want you regretting it in the morning."
"Britt, I know what I am doing. I know I have been drinking, but I am very aware of what I am doing and I want your cock in my pussy right now."
I did as asked, and we were both naked and fucking in no time. She was possessed. After I came the first time, she sucked me hard and we went again. We took a shower together and I had to get out of the shower to get another rubber. I had only brought six and I was afraid I would run out but after the shower, she wore down and said she'd had enough.
We decided to go to a show and she wanted to see a magic show so we got tickets through the concierge. It was a great show and April was very happy. She was drinking but I think she never really had the opportunity to be a little girl growing up, so as when we went to Disney, this was a big adventure for her. I felt like a parent taking delight in the child having fun. I did enjoy the show and then we went to the casino and I stood behind her and taught her how to play craps. She started with a $1,000 and was up around $4,000 before it started to slip away. When she got down to $2,000, I told her it was time to leave and she whined for a minute before I slid my hand under her short dress and grabbed her. I told her to, "Tell the dealer to color up your chips."
"Please color up my chips."
The dealer took her chips and gave their higher denomination chips so she wouldn't have to carry large stacks though the casino to the cage to cash out.
I said, "Now tip him $100 and tell him thank you."
She did as I said and we walked over to the cage to cash out. When we were in the elevator she said, "Why did you make me quit, I was having fun."
"I know you were having fun. Do you see all of the cool hotels, restaurants and shops all over Vegas?"
"Yeah."
"Do you think they were built so people could come and take their money?"
"No."
"The odds of winning any of the games over time are zero. You can be up for a while but statistically speaking you will lose if you play long enough. You won betting on horses and you won playing craps. You have new clothes, shoes and some fine new undies. You have a new suitcase and I paid for the flights, room and meals. We both are going home with more money than we showed up with and as far as you are concerned, I would say that $6,000 in your pocket is better than $4,000 after you lost the last two. You had fun so take the money and run."
"When you put it that way, I guess it was a good time to stop."
"I also have heard that it is bad luck to take home any unused rubbers from Vegas."
"You are so full of it. We could always just leave them here."
"I plan on leaving them here after I fill them with you."
"So you think you will get lucky huh?"
"If not with you there are plenty of women in Vegas. We can go out to a club or two and you can wait in the lobby while I make sure our luck is intact. We have $1,000,000 still riding on the Triple Crown."
"Well, I will have to do my part to keep the luck of the rubbers working."
We were not as frantic this time and I did about everything except take her anally. We woke around 9 am and went down for breakfast before packing to catch our plane home around noon. We got back to the dorm around 10:30 pm. I parked out front and she walked in with me. We dumped my bags in my room and then went down to see Reggie.
"Reg, I got this ticket in Vegas. I will sell it to you for $110. Do you want it?"
"What is it for?"
"This is a ticket for Affirmed to win the Triple Crown."
"He won yesterday in the Derby, where did you get the ticket?"
"April bought it for you, if you want it. If not she will keep it for herself."
"Do you think he has a shot? There has never been a back-to-back Triple Crown winner."
"It will cost you $110 to find out."
He took the ticket and looked at it. He said "210 to 1 for $100. I thought you said $110."
"April had to buy the ticket and then carry it all the way across the country for you. Is that not worth $10?"
"Do I have to go to Vegas if I win?"
"You can pay April to go for you. If I win I am sending my attorney."
"OK man, I hope I win." He went and got the money and gave it to April. She handed $100 to me and slid the ten into her bra. "Thanks big boy."
I walked her out to the car and she gave me a big kiss before she hopped in and headed for her place.
Two weeks later, she came into my room. I was working on a final paper for humanities and studying hard for finals. I had A's across the board and needed to do well on the finals to stay at that level. April said, "Come on."
"I am studying. What do you want?"
"I want to watch the race. It starts in an hour. Come get some food and watch it with me."
I had forgotten about it and asked her to see if Reggie wanted to go with us. She came back and Reggie was with her. I made them sit quietly for five minutes while I completed my thought and jotted some notes so I could remember the points I wanted to make.
We went over to Snuffy's. April remembered that we won the World Series bet there and she was superstitious. We watched the race and the top three in the Derby finished in the same order at the Preakness. Reggie was happy and April was on fire. She was screaming at the TV again and I was laughing so hard I had to watch the replay to see what actually happened. She was on my lap kissing me. I said, "I guess the lucky rubbers helped, huh?"
"Yep, we should get some more to keep the streak alive."
Reggie was looking at us as if we grew horns.
I said, "Reggie, we all know that if you leave Vegas with unused rubbers that it is bad luck, so April made sure that we had only good luck when we left."
Reggie smiled and nodded, "Thank you April, I should buy you some more to keep the streak alive for a few more weeks." We stopped by the drugstore on the way home and Reggie bought her a box. She was not embarrassed at all and held the bag like it was a winning lottery ticket. We were barely in the dorm when she said, "Bye Reggie." She pulled me to my room and we had to use all three condoms in the small box before she would go home for the night.
I spent the next week studying for finals and figuring out where I would live next year. I was going to take the summer off. April was going to move into an apartment with two girls from her dorm. Reggie was going to be back and he was taking my room. I could have stayed but wanted more space than my cell had to offer. I looked at the apartment where April was moving and found a small, four-unit complex of three-bedroom apartments. It had parking in front and a small pool with a privacy fence in back. I took the open unit on the ground floor. It was right under April's place. I was going just to put down my deposit. I had money and did not want to play roulette with a roommate so I took the whole place by myself. I decided to just pay for a year and leave it empty over the summer. Reggie said he would watch it for me so he could save on rent, and I told him that would be fine. It was a brick building with two upper and two lower units and a walkway in between. After my last class, April helped me pack my belongings into the Land Cruiser and move it to my new place. Reggie had a key and a car so he could move his own crap. April drove home with me to Orlando and flew home from there. It was a cheaper plane flight so her parents didn't complain at all. We drove home and I told her that if we won she would have to invite me up so I could drop off a check for services rendered.
She still had her copy of the contract. She spent the night on Thursday night and Doug drove with us to the airport on Friday. She was surprised when I got on the plane with her.
"What are you doing? My parents will freak out if I show up with a guy, unannounced."
"Chill out, baby, I am going to see my grandparents in Atlanta. You are connecting though Atlanta so I picked your flight."
"Cool. I will have to figure out what to tell my parents when we win the bet and you bring me the check."
Jerri
- 10.07.2022
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