Orgasm Diary September 2020
- 2 years ago
- 21
- 0
Monday when I got back from my workout, she was gone. I needed to settle back into a rhythm because I was already badly off, due to the trip to New York. I focused on my school. I went to class and came home to study. Shannon showed up and cleaned for me. It wasn't too bad and she finished in just over two hours. She did the laundry and asked why my shirt was missing buttons.
"Just throw the shirt away." I said.
"This is a nice shirt. I could buy some buttons and fix it for you." She replied.
"Shannon, do whatever you want. I have to study now. By the way, I told John to ask you to have a three way with him and Cathy. You better make sure you shave extra close."
"I liked it when Monica ate my pussy. I wonder how Cathy will taste compared to Amy. Thanks for setting me up. Benji wanted me to ask about swapping with Monica. I don't think he is having the luck that I am."
"Tell Benji that I had to go to New York and haven't seen Monica. I met a biker chick from Micanopy and an international studies student in New York who were good fucks if he wants their numbers."
"I'll let him know."
I paid her and sent her on her way. I needed to remember to get my $10 from April for the ironing.
Life went on. I skipped basketball and then tennis with John on Tuesday. I did play cards on Wednesday, and learned that Dottie had seen the lawyer and was going back to pick up the agreement on Friday. She was on the rag so I got a blowjob; we met some couples and talked about playing away from the center. I did play tennis on Thursday.
John said, "Hey, I asked Shannon about a three way. Well, I was somewhat not sure how to ask and then she said you had told her we might want to get together. She is coming over on Saturday. Mark is going home for the weekend."
I said, "I'm sure she will shave around her pussy so Cathy will have an easy time. You should shave Cathy to return the favor."
"Really?" he asked.
"I hate picking hair out of my teeth. I don't know about you," I said.
"I have never done that. Do you really do that?"
I said, "Every chance I get." Then I kicked his ass in tennis.
Friday, Monica stopped by and took one for the team. I asked about Dani and she said that she hadn't talked to her since last week. I told her to tell Dani hello from me if she saw her.
Monica said, "Britt, you know that my mom is my best friend. Well, I told her about what you said two weeks ago when you fucked me. She asked if you really wanted to fuck her next time, she came to visit. I told her that you would die with two sets of tits like ours and if she brings her sister; that your head may just explode."
"Tell her I would love to take pictures of all of you. You can bring Dani and I'll take some of her as well."
"I'll let her know," she said as she left to get ready for the party.
Saturday, I saw April for the first time since the trip. I said, "Hey, if it isn't 'love 'em and leave 'em, didn't wash my clothes, welsher of bets' girl."
"Hey, it is good to see you too, golf partner," was her reply.
"Where have you been hiding?" I asked.
"I'm trying to patch things up with my roommate. Did you do something to her? Whenever we start to get close your name will come up and she gets all pissy again."
I said, "She just wants my cock like every other female. Until she has it, she will be pissed at anyone else that has had it. It's the haves versus the have-nots."
"It is always about you, isn't it?"
"That is what you just said. Whenever I'm mentioned she gets penis envy."
"Shut up. Do you want to get lunch before we go to the course tomorrow?" She asked.
"As long as it isn't grilled cheese. It makes my hand greasy. I want to make certain that I have a good grip on my shaft."
"We can just stop at McDonalds and then all the grease will be in your stomach," she said.
"Let's just grab a sub."
"OK. We can leave at noon and then drive over and warm up after your sub."
I said, "Sounds good."
She said, "Penis envy, that's a good one. When I see her, I'll let her in on your theory. I'll get your $50, unless you want to go double or nothing on the penis envy theory?"
"I would take that bet," I said.
"I'll think about it. I gotta go. See you tomorrow at noon."
I worked at getting ahead again in school reading and then worked on a project for communications that was a month out. I also started work on an accounting project. When 9 PM rolled around, I was tired and hungry so I had two bananas and an apple with peanut butter and went to bed.
I was up early and was at Dottie's by 8 AM. She let me in and had eggs and bacon. She also had coffee. I ate the eggs and bacon in the kitchen and then we went out back to drink our coffee. I asked how she was.
Dottie said, "I went to see the lawyer yesterday to pick up the agreement. It is like a prenuptial agreement but it is more like a contract for you to perform a service. My child and I'll not have any rights to child support. You also give up custody rights so we can do what we want but the child will be mine."
I asked, "But did you shave your pussy?"
She blushed but nodded her head. I held out my hands to signal, 'What are you waiting for? Show me.'
Dottie stood and took off her shorts. She knew better than to stop there and removed her top as well. I had her sit in the Adirondack chair and put her legs up on the arms of the chair. I licked everything top to bottom side to side. I told her to hold her pussy open wide. She did and my face almost disappeared into her snatch. I tried to lick her cervix. I came up and clamped down on her clit. I sucked, nibbled, licked and gave the small nub a mini blowjob. She came and came so much that she had to bite her arm because she thought the neighbors would come to see what was causing the noise. The grass was a little wet but I put her on her back and said, "Now that we have signed the agreement, I can plant my seeds in your garden. I want you pregnant so when we swap with the Joneses from the card group, Mr. Jones won't knock you up on accident."
Dottie went off like a firecracker and I let the sperm fill her cunt. I told her that I had to go but for her to lie there for at least thirty minutes for the sperm to have a chance. She was lying there when I walked out and rode away.
I got a turkey sub and ate it in the car on the way to the course. I wanted to take the Harley but she voted on the Land Cruiser. We were early and we hit balls and then putted for thirty minutes. She had on her game face when we met on the first tee.
She said, "Hello Chris. Are you and Mandy ready to get your asses kicked?"
Chris couldn't even open his mouth before Mandy replied, "I got a new outfit from what we took off of you last time."
April said, "Would you like to raise the stakes?"
"To what?" she asked.
"We can play for the same cash but the loser has to give a massage with the happy ending. A thirty minute massage."
"If I'm going to get naked so Britt can finally say he touched a woman, we should make it an hour."
April looked at me.
"I was going to try to calm you two down until Mandy had to challenge my manhood. We should set aside plenty of time because after I get a one-hour massage it will probably take the inexperienced little girl another hour to get me off. She will most likely have to lose her virginity to do it."
Chris was speechless.
I asked, "Chris, are you in or do you want to can it?"
He said, "I'm not sure if I want to win or lose."
Mandy said, "You had better win or I'll kick your ass."
Looking back at the day, Chris and I split it nearly even but the extra putting practice and motivation had April dominating Mandy. The comments about how she will look good in the nude, rubbing a real man, had her flustered. April shot eight over and Mandy was closer to eighteen over. Chris had enough good holes so they were down net five just as we were, but on top of the $25 each, they had to give the massages. I was a good sport and offered to cook dinner and take care of the drinks.
I made sure that April wanted to go through with it. She said that Chris was cute. She said that she wouldn't let him fuck her even with a condom but she may give him a hand job for being a good sport. She really just wanted to watch Mandy deal with the humiliation.
I made chicken piccata for dinner, and the lemon accented the chicken well. I did make a salad this time and roasted some new potatoes as well. Mandy was hitting the wine pretty hard. Liquid courage was my first thought. I let April take the lead since I knew she wanted to watch but I figure she and Chris would go to the guest room.
Doyle skipped golf the next day. I had my money from the bank, so if I lost, I'd still be OK. From the previous day's results, they all saw that I only had won a single hole the entire day, so they offered me the same number of strokes. When the ball flew off my driver and soared high and straight down the fairway, I heard a couple of "oh shit's" from the rest of the foursome. My irons were still doing well, so by the end of the day I really cleaned up. They all accused me of...
I did my morning routine on Tuesday and saw the same swimmers. Dawn was out of the pool and drying off when I finished. We talked a bit about her classes and that the first football game of the year was this weekend. Then I went to start the day. I had scheduled all my classes, except one, on Mondays through Thursdays. I had a chem. lab on Friday. With this schedule I worked hard, studied hard during the week, and figured out what the lab was about ahead of time. I was still reading when...
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...
Mom and Bill had both been married before, so this time the wedding was going to be a small gathering. Dad was happy for Mom but thought it would be simply best to send a card and a gift. My grandparents came down and a couple of friends from Mom's work were there. Bill had his parents, two brothers, one sister, three nephews, two nieces and two daughters. He also had friends so there was better representation on the groom's side. With the small crowd, they decided to get married in the...
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The next morning, I did my normal workout ending with a run on the beach. As I slowed near the condominium I saw Mom sitting on the wooden steps at the end of the walkway that spanned the dunes between the condominium and the beach. She looked good and content with her cup of coffee and a slight smile as I walked up. She stood and asked if I was still up for a walk or if I needed a break. I took her coffee and had a sip. It was almost empty so I set it on the top step and took her hand...
One thing that did come up was that the school was using the Survival of the Fittest gym for many of their athletes and one of their new athletes was my first love or first fling, Jackie. She was a freshman on the women’s basketball team and thought she was something special. Jackie and I had never broken up because we were never officially together. After she and I were together, her dad started to be a little more lenient. She liked the sex we had and then seemed to go through half the...
I was planning on heading back to Nashville, but John had some things he wanted to go over with me, and Marshal wanted to see me about some things, so I spent Monday and Tuesday in meetings. Wednesday morning, I packed my stuff at Doug's, before heading up the road towards Gainesville. I showed up at my old apartment where Cathy, Darcy, and Dani were all happy to see me. We had a nice dinner together. That night, I knew that I had to please Darcy so we spent the night taking turns...
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We flew in on Thursday morning to get accustomed to the heat and time differences. Darcy had again gotten involved and the team was staying on the strip at Bally’s, the same place they kept a suite for times they didn’t want to drive home. The girls all shared rooms, the coaches had their own and I stayed in the suite. It was nice to be in Vegas but this time I felt more like a visitor than a resident. Patty found out about the large two-bedroom suite with living room and kitchen. After...
I woke with a nice wet mouth around my penis, and when I looked down, I saw Jill's head using my stomach for a pillow while Marion was taking care of me. When she saw that I was awake, Marion picked up the pace and a short time later she was sharing my spend in a nice kiss with Jill. We wandered out to the kitchen, and after a cup of coffee, I went back for my workout. Marion tried to get me to skip it since I was going to play tennis later, but I told her it was a habit that I planned to...
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While Missy fixed us lunch, Angus called to say he'd be late again. April and I spent the day chatting about our lives, and reminiscing about college. Missy heard about some of her daughter's activities, but it didn't seem to bother her as much as it embarrassed April. Around five, I let them have some time alone. I went back to the hotel, and when I getting out my address book to call Darcy, I ran across the name Mark Dunlap. It jumped out at me, as a memory from Angus' bachelor party...
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The wedding scene was beautiful with the lawn filled with white chairs leading to a small arbor beautifully accented with white flowers. The ocean played its role, as a splendid backdrop to the festivities. Doug was there to keep me from running away, and Karen looked great with her small bouquet of beautiful and fragrant flowers. Darcy had received offers from many of her orchestra friends to play at the wedding, and for a free trip to Bermuda, waved their standard fee. They started playing...
Beth came over, so we drank wine, and relaxed in the big family room. Brittany had to give every single person a hug and a kiss before Lilly could take her to bed. The talk turned to underwear, and Laura and Marny both raved about the support in their legs, and the support of the bra. After they talked about underwear for ten minutes, I asked a simple question, "Have you given this underwear company a name yet?" "Mary wanted to call it Mary's, but we vetoed that. We kicked around Happy...
As I ran, I thought about the coincidences that occurred during my life. I had met only two people named Chuck, and saw both of them on the same day on opposite coasts. There were two Karens that both preferred women, and two people who want to live and be with each other that don't have time for each other. I hope that Darcy is finding the satisfaction in her performances that she's looking to have. At this point in my life, time seemed to just flow by, and it was hard to keep up with it....
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I arrived at Kathryn's and Jill came out. She said, "What are you doing to my little sister? She is only a freshman." I said, "Jill I am not looking to marry her. We are just kids. I just turned fifteen and she will be fifteen in a couple months. I think she is cute in both her underwear and her bikini. Besides her sister is one of the prettiest girls in the school and she just wants to be friends. If Kathryn is half as pretty, half as smart and half as nice as her sister, then I will...
The more I thought about my business plan the more that I wanted to speed up the implementation and avoid the years of investing that it would take to save enough to do everything by myself. To make this happen, I knew that it was important for me to improve my organizational skills, gather all the data and finish the business plan. I had a professor for my finance class that was the head of the business department at the school. I stopped by during office hours to speak with Dr. Stahl. I...
At 8:59 there was a light knock on the door. I had on a pair of boxers and looked through the peep hole to see who it was. I opened the door and said, “Good morning Judy. Good morning Pam.” Standing next to Judy was her sister, Pam Jones. Pam went to school with me and was in the same grade. Her smile disappeared and her face went white as I swung open the door and Judy pulled her into the suite. Darcy had come over and said “What do we have here?” “This is my sister, Pam. I asked her to...
With the wedding coming up quickly, I felt bad that we couldn't invite a lot of our new friends and co-workers. As Darcy, Beth, and Lilly headed out to Bermuda to go over last-minute arrangements, they left me to play the role of a bachelor. Much to her dismay, Karen had to stay and work. That night, as we were riding home from the office together, I pointed her to the Frontier hotel. We went in and had a nice dinner. Karen wasn't afraid of men, but she didn't lust after them. We talked...
Johnny came by the next morning, and asked, "Did you quit as coach or is it your intention to just show up for the games now?" "Sorry partner, but I've been busy." "I know. Thanks for helping my mom. She's doing much better, and I can't remember her being this happy since Dad passed. We're going to Oregon this weekend, and then to Miami. Are you coming with us?" "I'll be there, and I'm bringing Lilly, so you can have your own room or we can see about getting a two-bedroom...
On the way back to the city, we talked about less important topics. We then walked a couple of blocks and had dinner. When we returned, Angus and April were waiting. They asked where we had gone and her mom told her the name of the restaurant. Angus thanked me again for coming up and thanked Missy for attending all of the services. They wanted to know if I wanted to go out with them. I said, "Angus, I'm happy to be invited but wouldn't you like to be alone?" April responded, "We have...
We stopped by the grocery on the way home and picked up some chicken and a waffle iron. I know they do the bone-in fried chicken but I like the boneless. I had everything else at the house. We both changed clothes and had started to set up when April stopped by. I invited her to stay for breakfast and told her the story of the morning race. I also told her that after breakfast she could clean up while I took Dani back to bed and fucked my new breakfast chef. April said, "Can I help?" Dani...
I got my workout done and I was walking back to my room to shower when I heard Beth say, "Come on, big boy, and give me that cock harder, baby, harder." I took a shower and then came out to fix some coffee and read the paper. I heard their door open and then heard the toilet flush and Beth came walking down the hall. I said, "Good morning, beautiful." "Hey handsome," was her reply. "I heard you calling my name this morning, I almost came in to join you two. I hope he pounded you...
She saw me and walked down. She said, "I saw you leave and thought you wanted some alone time." "No. I just wanted to make sure I was safe before I put you into harm's way. It was easy to learn so here I am. You may want to bring a towel with you so you can lie down. She went back and got a towel and her sunglasses. I was able to push the boat out again and made sure I had the boat pointed in the right direction before I hopped on and hauled in the sail to capture the wind and move us...
A week later, we flew back to Detroit and got the Toyota. We headed east. Doug asked where we were going; I told him I had a stop to make. I still had some time to relax before they finished the financing. Doug was dealing with the loss of his parents and I was going to try to help as much as I could. He'd gone through the shock of finding out his parents were gone. Denial had run its course along with pain and guilt. Being without parents or siblings and then having the business snatched...
Wednesday started with a blow job and a smile. We adjusted the workout a bit but did much of the same. She liked to jump with me since she had to work harder to reach my fingertips. I had to work hard to out jump her. I was consistently just over nine and a half feet so later, back at the condominium, I took a short string and attached it to the ceiling with a golf ball attached to it with an eye screw. It was just over 9’6” to the bottom of the ball. I would jump up and touch it and it felt...
After the Olympics, Patty, Mindy, and Eve all wanted to move to Vegas. Patty was going to take on the job that had been discussed a year earlier with Survival of the Fittest. Mindy and Eve wanted to open their own gym and coach new aspiring Olympians while Mindy continued to train Eve. Mindy had done well but was starting to feel her age at twenty years old. She didn’t want to work for four more years to grab at silvers and bronze medals. She was going out on top and would be back with Eve...
When we woke up in the morning, it was after eight and I knew that we'd missed Sam. I dropped down to do my push-ups while wearing my boxers. Paige had gotten out of bed and was watching me. As I finished my last push-up, I hopped up and swung my feet between my hands, so that I was in a sitting position. She sat on the side of the bed as I went through my two hundred-fifty sit ups. I started to break a sweat for the last hundred or so. Paige said, "I was wondering how you got to look the...
Yolanda and I had a fun weekend. It was the wrong time of year to have any crops in the fields, but I kept her as my kitchen worker. She made me promise that there wouldn't be any pictures, and I couldn't tell John anything. She is about twenty-five years older than me, but still in good shape, and very sexy with those huge nipples and round ass. I had her in the kitchen fixing lunch when I heard a truck pull up outside. I looked out the window and saw Jim White. Yolanda started to move to...
When we returned to Darcy's apartment, it was quiet, so we headed to her bedroom. As we were walking, we didn't have a need to talk. We took off each other's clothes and after quickly checking to make sure she felt well lubricated, I shifted my body, and I laid my body down between her legs. She grabbed me, and set my dick head in position. As I slid in her, a sound came out of her that was somewhere between a moan and a purr. The love and desire fueled us into a slow rhythm where I could...
That day didn't go as planned, but I care for Mary and her family. I hope that I didn't hurt her or lead her on so much that she thought that I'd actually do something with an eight or nine-year old girl. Beth wasn't upset with me, so I let go as I drove back to my condo. Christmas Eve is for last-minute shoppers. I had my list and some general ideas for most of my friends and family. A group of girl scouts made quite a bit by wrapping all the things I bought. I took most of them home...
The tournament in Dallas just cost me an extra three grand. I didn't want to keep the big ugly trophy and they wouldn't let me throw it away, so I had to buy a new trophy case to place in the office to hold the tournament things. The entire issue frustrated me, but it soon passed. Darcy was funny, because she was mad at the slut Wanda for trying to seduce me, but at the same time, she was horny for Melody. I guess I was also, and that's what made it funny. We were hypocrites when it came...
We didn't have a tournament this weekend, but we were going to Oregon next weekend, and then to Miami the following week. To catch up on things, I went into the office to see what I'd missed. The trophy case was already filling up, and someone had placed a team picture in the case as well. It was hard not to miss it as I went through the lobby. As I walked, I said hello to the security guards before ascending to the top floor, and my box of fun that they call an office. I felt...
After we hung up, I called a family meeting to let them know about the Forbes Magazine article. It was coming out at a good time since school was almost over for the year and I’d be traveling all over the world working on tournaments. Gloria was a quick study and learned the game of poker rather quickly as statistics were given out and position at the table compared to the dealer or an aggressive player should influence your strategy. She was going to stay at the house to work all summer....
I said, "Get naked." "What?" "I said, 'get naked.'" She looked at me silently for a moment, and then did what I asked her to do. When she was completely naked, I said, "Good girl." I had her sit in a straight back kitchen chair. I spread her legs and I touched her back, arms, and chin. I walked around her and then got my camera. I had her sit straight and tall with the legs spread and her hands on her knees. I snapped two shots. She was a beauty. I handed her pink panties to...
Darcy was sitting in a chair, naked, reading a textbook. She looked up and waved as I entered. I didn't want to interrupt her so I made a munching motion showing me eating. She stood and led me into the living room. She gave me a hug and said, "Thank you for my pet. I want to help her get in shape and make her my sex toy. The first thing I did was to teach her how to eat pussy. I still have not shaved her, but I will when she shows some progress. I put her on the scales and she weighs 145....
Patty graduated a week after I did and she was happy to see me in the audience when she came down off the stage. Her mom was there and sober. She had a job and was living with another woman. Darcy had made sure that she got the best treatment and that the woman that was sharing a house with her was qualified to keep her on the straight and narrow. Darcy had bought the house and was renting it to them at a deep discount. The lease clearly stated that any alcohol or drugs meant they were on the...
The next morning, I had Jay drive us to the airport where Linda had arranged a chartered flight for us down to Surat to meet with a loom manufacturer. Debbie had flown but never by private jet. Sophia had never been higher than the room she was staying in at the hotel. When we were in the air, they were both like little girls scurrying around to see something out one side or the other or check out the amenities of the plane. We did have a flight attendant and she was used to new flyers and...
The summer air swept clouds of thick black smoke through the grassy hills. In West Virginia, the air was hot and polluted enough already. His eyes stung, watering as he turned away from the fire. Pulling out a bandana, he spit before covering his mouth. Another crop was lost to rival looters, the third one this week. They'd taken as much corn and soy as they could before setting the bare fields ablaze. We have been at War for over 5 years now, with no signs of it ending anytime soon. He had...
It was Day 0 of WeebCon 2020, one of the most highly regarded anime conventions in North America. The badge pickup line was bustling with activity; eager con-goers exchanged stories, heartfelt hugs and video game friend codes. Cosplayers struck proud poses and friend groups swapped schedules. Not John though. He had come alone. This year, WeebCon had added a new feature to their VIP badge that he had initially not believed when he purchased it. For the duration of the convention he was a Harem...
Mind ControlThis all started when I noticed a stray cat crossing my property a few times. Apparently, that is all it takes. Beware!When I was in the Army, back in the early-to-middle 1980's, I was privilrgrd to know and serve under some sergeants who were Viet Nam veterans. One of them used to love to say, "Do you know what the difference between a fairy tale and a war story is? A fairy tale begins with, 'Once upon a time, ...' & a WAR STORY begins with, 'This is NO BULLSHIT, because I was THERE, and I...