My Best Friend's Moms Ch. 01

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Damn my best friend's Moms were HOT! Time to jerk off again.
4.5k words
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Part 1 of the 3 part series

Updated 11/15/2023
Created 09/15/2022
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OldMan45
OldMan45
1,033 Followers

My pitching arm was sore, not from ball practice, but from pounding my dick thinking about my best friend's moms. My last girlfriend dropped me, she said all I thought about was sex, well DUH! It took me a year dating her to even get her panties off, then when I pulled my cock out, she screamed no way was I putting that thing in her!

At least I got her to jerk me off before I took her home.

Yeah, I have a big cock, 9 inches and thick. I'm not a virgin, I did know a couple of older girls that were sluts, not so pretty in the face, but loved my dick. I always wore protection, I didn't want my dick to fall off from some disease. I learned a lot about fucking from Amy and Tammy, but I didn't want to be seen with them.

I had spent the last few years lusting after my friend's moms. I knew it was never going to happen, but it sure was nice dreaming of ways to take them as I jerked off.

"Dylan," my Mom hollered, "are you ready to go?"

"Yeah Mom," I shouted, "just give me a minute," as I cleaned my cock off with a dirty towel, and grabbed my swim truck and slipped them on. Throwing a beach towel around my shoulders and sliding some flip-flops on, I headed down stairs.

"Help me carry the potato salad and those 2 pies over there," as she nodded toward the kitchen island/breakfast counter. "Izzy (Isabella's nickname) is bringing baked beans and sodas for you boys."

"I know Mom, Mr. Carson, the gracious host is providing ribs, chicken, burgers and hot dogs," I said in a surly voice.

"Dylan DeWayne," she rolled her eyes at me, "watch your tone. Mr. Carson is a nice person and he always contributes to the baseball team. He loves you boys."

When Mom uses 'Dylan DeWayne' I know she's not happy with me. "Sorry Mom, but if I have to hear him tell us again about how great he was, and they won the State Championship when he played, and he drove in the winning run..."

"STOP IT, that's a rude thing to say. One day you will be older and have children, and I imagine you'll have stories you will tell your children. Maybe not in such a boastfully manner," she giggled.

"Yes ma'am, I'll behave, as long as you tell me there is another cherry pie your leaving here just for me."

"You know there is," she laughed, "don't I always take care of my favorite man."

We were the last to arrive, Mr. Carson and Mr. Thomas were outside at the grill drinking beer, Mrs. Carson and Mrs. Thomas were setting out paper plates, condiments, etc. on a table under a covered portion of the patio.

I ask where was Ben and Matt, and Mrs. Carson said in the basement. I found them playing X Box, "What the hell guys, it's beautiful outside, I thought we were going to swim."

Matt just glanced at me and winked, as Ben grumbled, "Dad was driving us crazy about how our team sucked the last two games," as he continued the game.

"Oh hell Ben, he just wants us to succeed. Don't be so hard on him. He did win the State Championship back in his playing days," I said as sincerely as I could without laughing.

"WHAT THE HELL DYLAN," Ben said, throwing his controller down, "are you taking his side?"

Keeping a straight face I said, "No man, but hell maybe we could learn something from him."

Jumping up off the couch Ben looked at Matt, "Are you listening this shit! Mr. Tripod is taking my Dad's side."

Matt broke out laughing, "Ben calm down, I think Dylan is pulling your chain."

Looking at me Ben saw I was grinning from ear to ear, "You think that's funny asshole, I'll pull all three of your legs off and beat you over your head," as he too broke out in a grin.

Sitting back down he said, "Sorry, he just really got to me earlier."

"Hey, Stump," my nickname for Ben, "any chance your Dad has some Bacardi stashed down here?"

"God," Matt said, "how do you two drink that sweet shit."

"Yeah I believe so," Ben grinned as he go up to go look.

"You should try it with coke Matt, it goes down real smooth," as I got up to follow Ben across the room.

"You don't remember that time you and Ben got me drunk on Rum and I puked my guts up," Matt complained. "I'll stick with beer, thank you."

"Boys," Mrs. Carson hollered, "the foods ready come on up and eat."

Ben found a case of Rum and gave me a thumbs up, then we headed upstairs. The Rum would have to wait.

As we ate I noticed the women, my Mom included, were all wearing one piece bathing suits and had their cover ups on. I thought to myself, hell my Mom was the hottest female in the room. What the hell I thought! I shouldn't have thoughts like that in my head! I wasn't about to perv on my own Mom! Just then Izzy stood and leaned over to grab an extra napkin and her cover up, fell forward giving me a nice view of her voluptuous cleavage.

I had just taken a bite of my burger and got choked, and started coughing! Stump reached over and slap me on my back laughing, saying, "Slow down Tripod, there is plenty of food, what's that your third burger."

"Honey, are you okay" my Mom ask.

"Yeah, I just swallowed wrong," as I wiped my mouth.

Mr. Carson laughed saying, "Careful son, when the the Thomasville Cardinals play the Yazoo Cougars, coach is going to need you on the mound. Ain't that right Frank"

"I think they will all be ready next week, the last couple of games they just had some bad breaks that cost them the games. It happens to the best of them," Frank said.

"Oh bullshit, bad breaks, you have to make your own breaks, I remember... blah, blah, blah," as Mr. Carson droned on.

Matt and Ben were rolling their eyes, but not me, Mom was staring at me. I just nodded when it seemed appropriate and pretended to be listening.

When he finished, I gave him a sincere look and said, "Your right Mr. Carson, when the chips are down it's time to suck it up and play harder."

"Well thank you Dylan, you hear that Ben, when the going gets tough, the tough get going!"

If looks could kill, I was a dead man, as Ben glared at me and choked out, "Yeah Daddy, your right as usual."

Matt put his napkin up like he was wiping his mouth to keep his grin hidden. My Mom was smiling at me, a proud smile I might add. Hell, there might be more than one cherry pie in my future. I was proud of myself.

We finished eating and Ben said, "Come on guys, let go back downstairs," as he gave me the evil eye.

"I think I'm going for a swim first, maybe later guys," as I grabbed my beach towel and headed to the pool. I thought it best to let Ben cool down after getting riled up about his Dad again. After swimming several laps, I was hanging on the side of the pool resting, when I heard female voices and looked up as the three women approached.

The petite Mrs. Carson was bending over placing her drink on a low table next to a lounge chair. Thank God, Mom and Mrs. Thomas had theirs backs to me. For a 46 year old woman Selma Carson didn't look a day over 30. Her blond hair was pulled in a pony tail, and her one piece swimsuit hugged her curves. From my angle just a few feet away, I looked up her legs to her tight round ass, and follow the red suit as it disappeared between her legs. As she stood up she pulled her cover up over her head, as she turned sideways to me, giving me side view outlining her figure and her perky breast pushing against the thin material. My cock was trying to climb out of the top of my trunks!

"Dang it, I forgot the sunscreen," I heard my Mom say, bringing my attention back to the situation at hand. The situation being my dick was seeking attention! I quickly slid back in the water and started swimming laps again. After five laps I was tired and my dick finally went down. Fortunately by that time all three ladies were settled in their lounge chairs all oiled up sunning themselves. Where the suntan lotion came from I could care less. I headed inside to find Ben and Matt.

Ben was on the phone with some girl named Sue, Matt nowhere around. "Okay it's date, I'll pick you up after church around one o'clock tomorrow. Bye."

"If your looking for Matt he went to see his girlfriend."

"Sounds like you have a hot date tomorrow, who's Sue?"

"You don't know her, she just moved in town recently. I met her at church last week and we seemed to hit it off. She goes to that private school Lake Academy."

"Wow, that's an expense school, but hell your Dad could afford it," I joked.

"Yeah, that's where he would send me, just for the prestige of it, if they had a sports program. Their idea of a sport is, the Debate Team, Chess Team or Science & Math Club." he laughed.

"Now tell me why you were kissing my Dad's ass earlier!"

"Hell Ben, my Mom heard me making fun of your Dad telling stories about when he played ball, and she came down hard on me. I was doing that to make her happy, and yeah, I guess to tease your ass," I laughed.

"Wants some Rum," as he got up and went and got some plastic cups and a 2 liter coke.

After 3 drinks a piece we were feeling a buzz, but hell Ben and I had been sneaking Rum drinks for several years and could handle it. His Dad drink the shit out of it, but didn't always know when to stop. Too many times he would drink until he went to sleep, and as big as he was you had to leave him where he happened to be.

We finish our drink and headed outside.

The ladies were in the pool now, and Mr. Carson and Mr. Thomas were watching TV on the patio. They were watching the St. Louis Cardinals vs Atlanta Braves, and Mr. Carson was already slurring his words.

Ben and I dove in the pool and listen to the ladies giggle and talk. They were on floating lounge chairs sipping Margarita's. With my Mom there and Ben, I tried not to perv on the ladies. I kept thinking down boy, I'll take care of you when I get home.

Mrs. Carson spoke up, "Ben dear, I need you tomorrow afternoon to help me move some boxes in the attic."

"Awe Mom, I have a date with that new girl we met at church last week," he groaned.

My Mom chimed in, "I'm sure Dylan could help you Selma,... couldn't you Dylan?"

"Yeah, no problem, I'd be happy to help Mrs. Carson."

"Thank you Dylan," said Mrs. Carson, "would around 2 o'clock be okay?"

"Yes ma'am, I'll be here."

"Thanks man, I owe you one," Ben said relieved.

About then Frank walked up and spoke to Ben, "Son, if you get out and dry off I believe the two of us can help your Dad upstairs, he's not very steady on his feet right now."

I glanced at Mrs. Carson and I could tell she was embarrassed and angry. Ben looked up and nodded and headed for the ladder. I started to follow and offer to help, but Ben told me, "No need Buddy, Frank and I can get him upstairs, I'll be back in a minute,"

I heard Mrs. Carson apologize to Mom and Izzy and say, "You would think a grown man would know when to stop drinking. Getting a buzz on is one thing, but getting falling down drunk there is no sense in it."

Mom and Izzy were trying to placate her, but what can you really say.

A few minutes later Ben was back, and Frank told Izzy they should probably be going. Izzy started to tell Frank she needed to help clean up, but my Mom spoke up and told her to go on, that her and I would stay and help pick up. After all we just lived across the street.

After they left Ben and I told our Moms we would clean up outside if they just got the things that went in the house. An hour later we had cleaned up outside and Mom and Selma had everything taken care of inside.

As Mom and I walked home, she was quiet and not talking. After we got inside, she stopped me and said, "Dylan, you do not go telling tales to your friends about Jake, or making snide remarks, you understand?"

"Yes ma'am. I won't,"

"Don't let Selma down tomorrow when you go over and help her. I'm going to get ready for bed, and remember that other cherry pie is in fridge," as she hugged me good night.

Damn. Don't think of me as a perv, but when she pressed against me to hug me, my trunks got tight! Hell I been exposed to 3 sexy women all day, and I couldn't get the image of Selma in her red bathing suit out of my mind. The hell with the cherry pie, I needed some time in the shower with my middle leg!

I was looking forward to helping Mrs. Carson tomorrow.

After returning from church the next day, Mom told me Selma had called earlier, and said to remind me dress comfortably, because it will be hot working in the attic. As I followed Mom upstairs to get out of our Sunday clothes, I couldn't keep from watching her ass sway with each step she took. My Dad, had been a lucky man I thought, too have landed a beauty like my Mom.

Yeah Jason DeWayne Davidson M.D. was lucky. Right!!! So damn lucky a fucking drunk ran a red light and killed him! Good thing the drunk died too, or I would have beat him to death with a baseball bat. That was six years ago, he had been on his way to meet Mom and I at the ball field.

Dr. J D Davidson started his OB-GYN practice with Mom running his office. He like to tell everyone that way the love of his life was always close by. Over the years the practice grew and eventually there were 6 doctors in the clinic. Mom in total charge of the office with four other ladies working the front office, along with several nurses. Mom and Dad always rode to work together, but that day I had a big game and was going to be the starting pitcher for the first time. Dad wanted to make sure at least one of them was there when I took the mound for the first time, so he had her drive her car that day so she could leave early. He would join us as soon as he could.

I remember walking off the field at the end of the 3rd inning smiling as the crowd cheered, I had just struck out the last three batters and we were winning 3-0. I looked up in the stands to see Mom, but I couldn't see her. I saw a cluster of people around someone laying on the ground, about that time Mr. Thomas threw his arms around me leading me off the field.

Later I learned a police officer came to inform Mom and she fainted, and that was the cluster of people I saw in the stands. Mr. Thomas had run to get me as his wife stayed with Mom. The next few days I barely remembered. The man that taught me to love baseball was gone. I quit the team, the hell with baseball! I didn't play anymore that year, but with Mom's encouragement I started playing the next year.

Dad had provided for us, Mom after a couple of months was ask to continue running the office by the other doctors and she finally agreed. Between the Buy-Sell Agreement settlement the doctors had set up, the Life Insurance money, the Insurance settlement from the other drivers carrier we were okay money wise. The clinic made Mom Office Administrator with a hefty salary increase, plus benefits including health insurance, 401-K etc. It was hard for her at first, but the staff and patients all loved her and within a year she was back to acting more like her old self. That's when she pressured me to return to baseball.

With a tee shirt, swimming trunks and a pair of running shoes on I headed over to help Mrs. Carson. I had been told to come on in and come upstairs. As I topped the stairs, Mrs. Carson yelled, "Up here in the attic Dylan."

The trapdoor was pulled down with stairs up into the attic, as I climbed up I saw Mrs. Carson kneeling and trying to move a box. She was wearing a pair of pink shorts that stretched across her ass and framed her cheeks. The sleeveless white top clung to her back from sweat, and her hair was piled on her head in a bun.

"Here, let me get that," I mumbled. "Where does it go?"

"Oh, that one," as she used her forearm to wipe sweat from her brow, "is going downstairs."

The box was marked 'TOYS' and I chuckled, "Is Ben going to start playing checkers and 'Go Fish' again."

"No," she laughed, "I giving some of this stuff away, but I am keeping things he might want to give his kids, if he ever has any. We have accumulated so much over the years, and things we will never use again needs to go."

"You just rest and tell me what to do, okay"

"Well, over there are boxes of old Xmas decoration, they go downstairs. Plus, over there," she pointed, "are several boxes of small kitchen appliances that go."

As she pointed and looked in that direction I could see the sweaty top cling to her chest, and could see the outline of her bra and her nipples making dents in shirt. I need relief I told myself.

"How about you rest and grab us some water, while I move those boxes out of the attic."

"Okay," as she whipped her brow again I watched her breast move as she breathed in and out, "I'll be right back."

When I was descending the ladder with a box balanced on my shoulder I didn't realize she was standing there watching until she spoke. Turning in her direction without thinking, my boner was right in her face! I heard her gasp then turn away saying, "When you put that down, here is some water. You look like you need to cool off."

Sitting the water bottle on some boxes I already stack up, she scurried down the hallway and I heard her say, "I just thought of something.. I'll.. I'll be right back."

Sitting on the floor where I could see if she returned, I held the cold water bottle against my boner trying to get it to go down!

We quietly worked another a hour and had all the boxes moved to the garage. She hadn't said much except what was necessary, like put those here or whatever. When it was finished we were both soaked in sweat.

"Lets go outside," she said, "and cool off. I'll get you another water, or coke, or whatever you want."

"Sounds great to me," as I started pulling my Tee shirt off, "maybe you could put a little Rum in my coke," as I started to the pool.

"Dylan DeWayne," she giggled, "your Mom would kill me if I gave you alcohol."

"I won't tell if you don't," I called over my shoulder.

Hanging my tee shirt on a chair, I kicked my shoes off and dove in the pool. Damn that felt good. Swimming to the shallow end I stood and was pushing my wet hair back, when Selma came up and sit on the top step with her feet in the water.

"Here," she grinned, handing me a red plastic cup, "I'll say you must have got it when I wasn't looking."

Sitting down a couple of steps below her I took a long swig of my drink. The lady does know how to make a drink I though as I said, "Thanks Mrs. C, are you sure there's not anything else I can do for you."

"Sorry I took your afternoon away from you, but thanks," as she took a big drink and sighed.

Tilting my head back to look at her, she had a sad look on her face. I stood up and sit my drink on the edge of the pool, then took hers and sit it next to mine. She had a funny look on her face as I picked her up under her arm pits and quickly turned and threw her in the pool. She didn't even have time to yell as she splashed down and went under.

She came up coughing, "What the hell Dylan," as she wiped the water and her hair out of her face.

"Here, give me your hand," I told her as I pulled her in shallow water where she could stand. "Sorry I shouldn't have done that, but you looked so damn sad sitting there, I thought maybe that would snap you out it. My bad,"

"I looked that bad huh," she grinned. "But yeah now I looked like a drowned rat," she laughed."

"You could never look bad on your worst day Mrs. C., but it's good to see a smile on your face again."

Pushing my luck I picked her up and sit her on the edge of the pool where the water was about 3 feet deep. "Stay, I'll get our drinks."

I didn't crowd her as I handed her drink to her. She was blushing as she took a big drink. She looked so cute and beautiful sitting there soaked, her clothes clinging to her. Her top almost transparent and I could see her 32A cup tits plain as day, her nipples were hard and she was breathing rapidly. The pink wet shorts hugged her tightly and you could see the outline of her bikini panties. My cock was harder than it's ever been, and I saw her looking at it.

OldMan45
OldMan45
1,033 Followers
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