Mom's Affair with My Best Buddy

I guess I was normal in high school. I had a bunch of buddies that I hung out with. There were the standard social events, but there was one event that really changed my life during this period. My dad died in a car crash. My mom and I were devastated. Fortunately for us, my dad had a ton of insurance, so mom could pay off the house and she didn't have to get a job for us to get by. It was a nice house actually. It had several bedrooms and even had an in-ground pool in the back yard. Compared to other families, we were pretty well off. Even with the comfort that he left for mom and me, there was that gap in the household with dad's passing.

I buried myself in school friends and activities. I was pretty good on the baseball field and I owned first base. All of those activities and the pleasures they offered were wiped out when I returned home each afternoon. My mom was depressed at loosing dad and she just couldn't seem to break out of it. Each night I'd go to bed in the room next to her bedroom -- the room she'd shared with my dad -- and I'd hear her sobbing. It was at least six months before the crying stopped and she seemed to be feeling better.

I didn't know how to support her in this period of our lives. I did the obvious and told her to get out of the house and do stuff. She finally took that advice and started to socialize with three women she'd met at a grief support group. Soon, the women left the group and started their own social activities. They'd go drinking. Not like getting shit-faced drinking, but social drinking.

She was dressed ready to go out with the ladies when she came into the kitchen where I was fixing some dinner for myself.

"So, I was wondering," she hesitated and then continued, "I was wondering if you thought it would be okay if I started seeing other people - men. I miss your dad, but I'm still lonely. If you think it's too soon or think people will talk, just say so. I just want to," she said and stopped mid thought.

"Mom, it's okay. I think it's great that you're ready to go on with your life. You're a young woman and you need a man in your life. I get it. And, if you are happy, I don't care what other people say."

She gave me a hug and a peck on the cheek and left for her outing. It was just a couple of weeks later when she said that she'd met a nice man named David. I figured that she'd met David before she asked for permission to date, but I let that pass. Lynda, that's my mom, started going on-and-on about David. He was good, and kind and funny and handsome and so much more. I didn't know if she were trying to convince me or herself.

"I've invited him to dinner on Friday and I'd like for you to meet him."

"Sounds good. Yep, Friday is good."

Friday came and so did David. He seemed nice enough. My late dad was the only yardstick against which I could measure a man dating my mom. David was a little younger than dad by a couple of years. He was taller, maybe six-two with brown hair with a bit of gray creeping in. He was very athletic looking. He had a big smile and seemed very comfortable meeting me.

We all talked over dinner, he was interested in me and my background -- I guess to win me over -- and my mom kept pointing out his good points every chance she got. Bottom line was that he seemed okay to me. If my mom liked him, then great.

Dinner ended and I put the dishes into the dishwasher and begged off for a school event. Leaving, I gave my mom a wink to show my approval of David. Her smile was one of delight and relief. I took my exit.

I got home a little after eleven from school and took a shower and got into bed. It wasn't long before I head sounds from my mom's room. Our bedrooms shared a wall. I couldn't make it all out, but I could make out my mom's voice. The other voice I determined was David's voice. Damn, that was quick. They were already in the fucking part of the relationship.

It wasn't long before I could hear the sounds of some serious fucking. It was odd, as I'd never heard this amount of noise when my father was alive. Back then I may hear a little noise from the bed, but this was different. This David guy was breathing hard as he made the entire bed shake and mom was voicing moans and little passion grunts. I even caught her telling David to "fuck her harder" and from the sound of it he did just that.

The thought of my mom in the next room fucking this David guy and apparently in a much more exciting way that had my father, was kind of exciting

Their fucking ending shortly afterwards with my mom actually screaming her passion and David shouting that he was going to "cum like a motherfucker". Everything went quiet -- for an hour or so. Then they started up again. I could not remember my parents fucking more than once in a night.

The next morning was Saturday and when I got up, mom was dressed in her bathrobe in the kitchen making breakfast. I entered and she looked uncomfortable.

"I guess you heard."

"Sure did," I said and smiled at her.

"We really hadn't planned for him to stay the night, it just happened and I'm glad that it did. I just hope it didn't upset you."

I decided to tease her to let her know I was okay. "So," I said, "did he cum like a motherfucker?"

She blushed. "So, you heard that, did you."

I laughed out loud and the tension was broken.

"Actually," she continued, "he does cum like a motherfucker and so did I."

"So, I guess we'll be seeing more of David, the cumming motherfucker."

"Damn, I hope so," mom said.

In fact, she did start seeing more of David. He had his own place but slept over at our house a couple of nights a week. And, their lovemaking got more energetic and noisier.

Spring of my Junior year rolled around and I was fully engaged in baseball. Mom, and often with David, would come to the games. Mom got to know most of the players and with summer soon to follow baseball season, we'd use our big back yard and pool to entertain the team. David who was still in the picture didn't make most of the parties as they were afternoon and early evening and he had his own schedule.

I was never sure if the guys came for the free food, the pool or to stare at my mom's tits. She sometimes caught them and they'd go bashful.

It was in the fall of my senior year that I met my new best friend, Randy. On the first day of senior year, the homeroom teacher called roll and everyone was asked to call out their birthday as a check of the school records. Randy and I had the same birthday, October seventy. That was enough to start a conversation later in the day. It seemed that both of us had missed the cutoff date of September thirtieth and we'd been held over a year before we could start first grade.

October seventh of my senior year - I was eighteen; Randy was twenty. Our lives were all changing.

Randy had a past. He'd been expelled two years ago -- for reasons that neither he nor the school would disclose. Now, after two years working shit jobs, Randy had returned to finish his senior year and get his diploma. He'd also returned to play a little baseball for the team. Randy, now twenty, had filled out looking more like a man than a high school guy. The guys on the team always gave him shit in the showers. "Hey, Randy, I have a date this weekend, could I borrow some chest hair?" He also was teased because he had the biggest cock any of us had ever seen. It had to be seven inches long and it was very thick. And, he had big balls too. Soon, he and "it" were known as Randy and peewee. "Hey, Randy, is peewee getting any pussy?" And, in the classic retort, he'd reply, "Yeah, peewee and me are fucking your mama tonight. She says that every man in her house has a little dick." Everyone would laugh and move on to something else.

David, mom's boyfriend, was not as often a visitor as before. By November, David was out of the picture.

When school ended, my mom and I planned a baseball celebration for our taking the district championship. It was June, and the water in the pool was still a bit chilly, but the guys didn't seem to care. The guys loved looking at mom's tits and several of them got hard-ons. Embarrassed, they'd either jump into the pool or move away or sit in a chair to wait it out.

Randy really liked looking at mom's boobs. At one point he came out of the pool next to her chair. He was pretty much full hard-on. His swim trunks did little to hide his cock. Instead of hiding it, he walked over to where mom was sunning herself and stood next to her.

"Hey, it's getting too hot to just sit, come and jump in the pool with us. Cool off."

With his big cock so apparent, she stuttered and declined.

Randy took her by the hand and lifted her from the chase lounge. Once she was standing, he picked her up, took her to the pool edge and he jumped in with her in his arms. They went under together and came up together. They both burst into laughter. What I only found out later was than while they were under the water, Randy had fondled her tits.

She had taken a spot on the edge of the pool and Randy asked her to do laps with him. She declined, but he started by himself. After several laps of the pool, he joined her at the edge. I couldn't hear what they were saying but there was a lot of laughter and giggles. It was obvious to me, and I hoped no one else, that my mom was flirting with Randy. How embarrassing to have them see my mom flirting with my best buddy.

Mom said that she was ready to get out of the pool and Randy put his hands on her waist and easily lifted her out of the water and onto the apron of the pool. He followed her out of the pool with a one hand leap. They both were dripping wet and Randy's bathing suit gave away his cock. Neither of them seemed to notice or care about this spectacle. They walked to her lounge where Randy picked up her towel and helped her dry off.

"I'm going to go in and bring out some more beer," mom said.

"I'll help," Randy said in the tone of a gracious guest at a cocktail party.

They walked inside. After several minutes, I decided to go in and see what was taking so long on the beer. When I entered the kitchen, I found mom facing the island with a six pack of beer in front of her, and Randy standing behind her pressed against her. His hands were caressing her abdomen. Standing this closely, I knew that his cock was pressed against her back.

"I'll help with the beer," I said and they both looked self-conscience and introduced some space between them. Mom grabbed the beer and walked toward the door and the pool. Randy started to follow her and I stepped in front of him.

"Randy, quit sniffing around my mom's pussy. Fuck, man. She's my mom! Promise me you'll leave her alone."

Randy's gaze moved from looking at me to looking beside me toward the pool. He was obviously enjoying seeing my mom wiggle her ass as she walked back to the pool. "We'll see." He said flatly with no emotion.

Mom had retaken her lounge chair and when Randy got back to the pool, he grabbed a beer and pulled his lounge chair next to hers. They whispered, who knows about what, back and forth between them. To me, it was obvious that they were flirting. I looked around the pool at my other friends. They were playing in the pool and didn't seem to notice the foreplay going on so blatantly on the edge of the pool.

Late afternoon came, my other friends left and I was relieved that they'd not see any more play between Randy and mom. Randy kept his seat beside mom and I kept mine a few feet away to watch them both closely.

Mom asked him to put more suntan lotion on her and he gladly agreed. He spread the lotion over her legs then slowly rubbed it in. Each time his fingers reached the bottom of her swimsuit, he slid his fingers slightly under the suit. It was obvious that he wanted to finger her. Mom did nothing to ward him off. He finally moved to her neck and upper chest. He had grown bolder and didn't stop at putting lotion on her cleavage, he slipped his hand into her suit cupping her breast. He squeezed her tit and she threw her head back and smiled. I couldn't believe that I was watching my mom let my buddy play with her tit -- in front of me! Finally, the lotion was put aside and they both relaxed into their chairs.

After another hour, my mom sat up and said, "I need to fix dinner. Randy, why don't you stay?"

He nodded his acceptance.

"I'm thinking something simple like hotdogs and some sides. I'll get started."

Again, playing the part of the gracious guest, Randy hopped up and offered to help and followed my mom into the house.

It had been at least twenty minutes and mom had not called me for dinner. I got up from the pool and walked into the house. There was no one in the den or kitchen. The kitchen counter had no evidence of a meal having been started. It was then that I heard sounds from down the hall. I crept along trying to be very quiet. The door to my mother's room was open. I looked in and saw Randy facing me with his hands on his hips and mom on her knees sucking his big cock. Randy smiled at me and held up to thumbs up to me. Her hands roamed his young athletic body. She ran her fingers through the hair on his lower abdomen, across his tight ass and down his thick hairy thighs.

"Babe, that feels so good. You're a really good cocksucker!" Randy was addressing her, but looking directly at me. "Can you take any more of me?"

I could hear slurpy sounds from my mom as she took as much of his big cock into her as she could. "Babe," Randy said, "can I have a little bit of your pussy now?" Without taking her mouth from his cock, she nodded her agreement.

He helped her stand and removed himself from between her and the bed. He positioned her at the edge of the bed with her chest on the bed. I realized that he planned to fuck my mom from behind, doggie style. He was actually going to fuck her like she was his bitch. I started to pull him away from her and kick his ass out of the house. I hesitated only when I heard mom tell him that she wanted him to fuck her with his big cock. I remembered that I'd said that she could date, but when I said that I didn't think that she'd be fucking my high school buddy.

"Randy," she said, "I stopped the pill a few months ago, so you'll have to pull out before you cum."

He didn't respond.

In her new position at the edge of the bed, I was now facing my mom's pussy. I'd never seen it before, of course, but now I was about to see more -- not just her pussy, but her pussy being fucked by my best buddy.

Randy was now in profile and I could see his massive cock standing erect. He looked even larger than he had in the shower at school. And, his shaved balls now looked enormous. Randy reached out and rubbed mom's pussy with the flat of his hand. I heard her moan and encourage him. Moments later, he spread her lips with is middle finger and placed his finger tip on her clit. She tensed and then he started to swirl his finger around her clit. She adjusted her stance, putting her feet a bit farther apart giving him easier access to her. He pulled her lips apart exposing her tender pink inside. With her pussy agape, Randy looked at me and I knew that he was doing this to torture me. It was working. Randy continued to rub her mom's pussy. She was getting more excited. I could hear it in her moans.

Randy used the fingers on one hand to hold her lips apart. He looked at me where I watched from the doorway. Using his other hand, me pointed at his massive cock with his index and middle fingers and then at mom's pussy. Then he plunged those two fingers into her pussy and started moving them in and out. I slumped to a sitting position in the doorway as he roughly fingered my mom. I knew it wouldn't be long before he'd have his cock in mom's pussy.

"Babe, you're really wet. You're dripping wet," he said to her and he winked at me.

"Fuck me now. I can't wait any longer. I need that cock in my pussy!"

Randy took the flat of his hand and slapped her pussy lips. I could hear the wetness with each slap.

I'd been so involved with the situation between Randy and mom that only then did I realize that I was hard as a baseball bat. Sure, I'd jerked off listening to mom and dad and then mom and David fucking, but this was totally different. My best friend, Randy, was about to fuck my mom right in front of me. I unfastened my swim trunks and slid them off sitting naked on the floor in the doorway. My cock was in my hand as he turned to fuck her.

Mom was shorter and Randy was just over six feet, so he moved his feet outside of her feet and bent his knees to lower his cock to her position. I could see between his legs as he positioned his cockhead at her pussy opening and pushed forward. I heard mom scream with pleasure. With my mom grunting and moaning, he drove his cock into her stopping when his balls were against her lips.

"I've never felt anything this wonderful," mom cried out. "I love your cock. It fills me like no other -- I love you inside of me."

His hands were on her hips as he started to piston in and out of her in smooth even strokes. She was obviously enjoying his fucking her. He grunted, squealed, and constantly moaned with passion. At that point, Randy raised his fist into the air and flipped me the bird.

It all seemed too much. I was sitting there watching my best buddy fuck my mom from behind like she was a bitch dog and she was loving it and asking for more. I looked down and realized that I was stroking my cock hard and fast. Mom was screaming like she'd never been fucked this good before and Randy was plunging his cock in and out of her.

Suddenly, mom began making different sounds and I realized that she was going to cum. She quit panting and held her breath as she beat her hands against the bed. Finally, she resumed breathing with a gasp. Between Randy's legs I could see him thrusting into her and escaping her was a fresh stream of her juice. Randy's balls were covered with her juice to the point that the juice was dripping from his balls.

My hand was tightly gripping my cock now wet and slick with pre-cum. I realized that I was pacing Randy's thrusting into mom. I felt my balls contract and I erupted in a huge cum that shot all over my chest. It was the most powerful jack I'd ever had and my cum kept coming.

My mom was still making passionate sounds and asking him for more cock. I wondered how long he could fuck before he came. It had already been at least twenty minutes since he sunk his cock into her. She was now starting her second cum. This time, her only sound was an almost continuous scream. A passerby may have heard her and thought she was being killed. But I knew that this was all pleasure and that this was a sound I'd never heard her make when dad or David were with her. Randy had taken her to another place of pleasure.

Randy's pace faltered. I saw his balls start to move inside his ball sack. He paused his thrusting with his cock fully engaged inside my mom. I saw his ball sack twitch with each delivery of his cum.

"You weren't supposed to cum in me!" Again, Randy said nothing.

Randy pulled back and the head of his cock slipped out. It was still dripping cum. He rubbed it against her pussy and her now engorged pussy lips and then pushed back inside her preventing the escape of his cum from her.

My own cum was running down my naked chest. I grabbed my swimsuit and wiped myself off. I crept away from the doorway. The last thing that I wanted was for mom to know that I watched, and jacked off, to she and Randy fucking.

I pulled on my cum-drenched swim trunks knowing that I couldn't explain a clothing change. I ran outside and jumped in the pool. Here in the pool, the cum was washed away.

Randy, strolled out of the house and over to me. I pulled myself out of the pool. Walking up to Randy I stood inches from his face. "I told you not to fuck my mom and you did anyway!"