My Friend's Mother Pt. 01

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Playing the dirty edition of "Would You Rather?"
4k words
4.46
46.9k
73

Part 1 of the 2 part series

Updated 06/11/2023
Created 06/07/2022
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Part 1 - It's all fun and games.

About a decade ago, my friend Austin and I graduated high school and it was the start of the summer.

It was the first Friday since school had ended and Austin sent me a text, inviting me over for the weekend to celebrate graduating high school.

Him and I met in elementary school and became close throughout middle and high school. We both spent the night over each other's house very often as we grew up and we had grown very comfortable around one another. We were practically inseparable all throughout high-school like two peas in a pod.

My parents and his were very familiar with each other and their home was like my home away from home. I always preferred to go to his house because he had a pool in the backyard and always had the newest video game consoles. Both of our dads were in the military, but I think his dad was a few pay grades above my dad.

I eagerly packed my bags, the night I received his text, making sure to include more than a handful of outfits. From a pair of gym shorts to a pair of slacks and everything in between, I made sure I was ready for any occasion.

The weekend came and I was there at Austin's house. We were in his room playing video games and his dad knocked on the door.

"Come in." Austin said, raising his voice over the sound effects of the game.

"The food will be here in 10 minutes. We also have a few board games and a game my buddy recommended we play." Austin's dad, Bryan said.

"Ok dad, sounds good." Austin quickly said as I was starting to gain the lead on him. His dad must have distracted him in the little time they were talking.

Before we knew it, the doorbell rang and we were on our feet. We paused the game and made our way downstairs and to the table.

"You're lucky we have to eat or I would have beaten you." I said to Austin jokingly.

"Yeah only because my dad was distracting me." Austin replied.

We had always been competitive when it came to gaming and we didn't hesitate to talk trash to one another, but it was all fun and games.

Bryan placed a few boxes of pizzas on the table along with a tall 2-liter coke and a few board games. Dallas, Austin's mother, sat at the dinner table and looked through the games.

"Looks like we have Yahtzee, Scrabble, and Would You Rather (Dirty Edition)?" Dallas announced, seeming to question the last game.

Dallas continued to question her husband Bryan saying, "Bryan are you sure this is appropriate for us to play with the boys?".

"Honey, Austin turned 18 in January and Jeffery turned 18 last weekend. It's time we started treating them like the men they are." Bryan said as he cracked open a beer for himself and sat down.

"Well you may as well get me a beer too, honey. Lord knows I'll need it." Dallas said helping herself to a couple slices of pizza.

I always seen Dallas and Bryan as a second set of parents of my own. So I was just as taken back as Dallas was about playing the game. We all helped ourselves to pizza and we were eventually on our way to playing the dirty game.

Bryan read the important part of the instructions out loud stating, "Each player will draw one card and it will be up to the player if they would like to answer the question or not. If they choose not to answer the question, they will have to do a dare the players decide on."

Bryan continued, "The dare for Dallas and I will be to take a shot and you guys will do 20 pushups since the both of you are underage."

Dallas eased out her seat saying "I'll grab the tequila."

A little disappointed, I chimed in, "That's it, 20 pushups?"

I had always been on the athletic end of the spectrum. I played sports all throughout high school and I did pushups every night before going to bed. I wasn't the most muscular, but I was well put together for my age.

A smirk overcame Bryan as he said, "We can make it 50 pushups, if you'd like Jeff."

"50 push ups? 20 is enough." Austin said interrupting. Austin was more of the smart and artsy one out of the two of us. He didn't play sports throughout high school but he also wasn't a push over. He just didn't care much for sports.

"Ok. I guess we will stick to 20 pushups." I said sounding a little bummed.

"Or maybe you can do 50 pushups and Austin can do 25, if you guys choose not to answer the question." Dallas cheerfully suggested.

I felt I might have bit off more than I can chew. Some I only did 100 pushups a day, I figured I might want to answer as many questions as possible. It would be in my best interest to space my sets of 50 push ups out as well as I can or I may not make it very far.

I accepted her challenge saying, "Sounds like a plan." I felt eager to show them all I can do 50 pushups and I couldn't back down from the challenge.

Austin drew the first card while biting off the crust of his pizza, "Would you rather go to the grocery store in your underwear or go to the beach nude?" He read aloud.

If you were a fly on the wall you would see everyone chewing their food, thinking what they would do themselves.

"Ah, thats easy. I would go to the beach nude. I would be able to swim the whole day and no one would ever know I was naked." Austin said with a smart tone.

Bryan laughed out loud almost choking on his pizza saying, "You will look like a dried up raisin when you're finally done swimming."

Dallas snickering chimed in saying, "You could call me, I'd bring you a towel and some shorts."

The thought of his mother possibly seeing him naked at the beach must have embarrassed him because he began to turn red.

I couldn't help but laugh at Austin's embarrassment saying, "At least you would have had underwear had you picked the grocery store scenario."

"Can I change my answer? I didn't think about that." Austin said feeling like he picked the wrong scenario.

"Its too late." Bryan said as he drew the next card. Without hesitation Bryan read his question out loud, "Would you rather sleep with your partner's siblings or your best friend's siblings?"

Bryan let out an, "Umm.." Which was followed by a long pause lasting a few seconds.

Dallas puts her beer down and crossed her arms, "Well?" She questioned her husband patiently waiting his answer.

"Oh! I'd sleep with my best friend's siblings, without a doubt." Bryan confidently said, thinking it was the right answer.

"You would do what?" Dallas asked, scolding her husband.

"I'm just answering the question, babe. I would never sleep with anyone other than you." Bryan said attempting to comfort his wife.

Austin's mother, Dallas, drew a card next with an attitude and continued to read her question out loud. "Would you rather sleep with your partner's friend or your child's friend?"

Dallas instinctively looked at her husband, thinking of his friends and shortly after looked at me. She immediately looked down in her lap after looking me deeply in my eyes, blushing. Everyone at the table knew what her answer was based on her body language but nobody said a word. Austin looked away himself letting out a deep sigh.

For the first time, after hearing Dallas read that question, I looked at her in a sexual way. When she looked me deeply in my eyes, I felt chemistry between her and I in a way I never felt before.

After our eyes met and she looked towards her lap, I looked at the wall to my left. I began imagining looking her deep in her green eyes as she sucked my penis.

Curiously, my eyes landed back on her and eventually my eyes landed on her breasts. Her nipples were piercing through her button up shirt and I noticed her hard nipples.

All within seconds, Dallas lifted her head and took a drink of her beer. She also poured herself a shot and took it. I now began looking at her through a new perspective and I was caught in a daze staring at her hard nipples through the fabric. I could feel an erection forming in my gym shorts as my penis laid stiffly on my thigh.

I was startled when Bryan said, "Jeff, it's your turn." I totally had forgot we were playing and I wondered if he had seen me staring at his wive's breast. I imagined her breast having to at least be a c-cup and it looked like she wasn't wearing a bra under her pajama shirt.

I drew a card and it read "Would you rather drink a glass of urine or eat a teaspoon of poop?" Without hesitation I got out of my chair and started doing pushups. The three of them counted out loud in unison until I reached 50.

I stood up trying to catch my breath. I must have worked up a sweat and I wiped my forehead with the tail end of my shirt. I began to pace the floor and used the tail end of my shirt to fan my upper body. I stood there for a second facing the table as I wiped my forehead.

"Jeff, have you been in the gym?" Dallas asked as she sipped her beer. I looked up and noticed Dallas was looking at my torso and for a second it even looked like she was looking at my crotch. Following her eyes, I looked down at my lap and noticed my abs and hard penis were on full display for Dallas and Bryan. Austin had his back to me and we were across from his parents.

I didn't know what to say and I sort've froze. Bryan took a good look at his wife and said, "Jeffery, why don't you have a seat? Those 50 push ups must have you beat."

I took my seat wondering if Dallas liked what she was seeing. I was starting to like this game and I was eager to continue playing. I kept an eye on Dallas' breasts as the game went on hoping to catch a look at her cleavage.

Austin took the next card reading it for us, "Would you rather your parents catch you having sex or catch your parents having sex?" Austin palmed his face and I started to realize Austin was a bit of a prude. I had never seen this side of him and it was funny.

Austin got up and assumed the push up position. He worked out the first 20 with ease and struggled with the remaining 5. We all rooted him on as he finished.

"Son, we have got to get you in the gym. You should be busting those out like Jeff." Bryan said sounding like he was disappointed in him.

"Oh hush, you're probably even more out of shape than he is Bryan." His wife rebutted.

"Yeah right Dallas!" Bryan responded sarcastically as he reached for the next card. "Would you rather catch your partner cheating or be caught cheating?" Bryan read.

Bryan responded by pouring a shot as his wife glared at him while drawing her card. He took his shot and looked at his wife as she stared him down.

"Would you rather swallow or spit?" Dallas read out loud to herself and the rest of us.

"Ew. Come on, Mom! Do we have to play this game?" Austin said ready to quit.

"I know what she'd rather do." Bryan said smirking to himself.

My eyes were on Dallas and I couldn't take my eyes off of her. For once I was attracted to her and I gave her lips and breasts an equal amount of my attention. I always knew she was a pretty woman but I never once thought of her sexually.

She stands 5'8" tall and is roughly 150 to 160 pounds. Her dirty blonde hair hangs down to the middle of her back. Her slender nose, high cheek bones, and full lips was now starting to catch my eye.

I was so hard and her reading this question stirred up something within me. Would she rather spit or swallow? Hell, I would love to know myself. I naturally began imagining her sucking my penis and swallowing my cum. Chills ran up my spine as I thought of my friend's mother in this way.

She smiled looking at her husband and begin pouring her shot. Damnit, I wanted to know if she prefers spitting or swallowing. Judging by how Bryan sat back in his chair smirking, I'm guessing she swallows.

I drew a card as she took her shot, reading it to everybody. "Would you rather talk dirty with the person on your left or right?" I naturally look at Austin, to my right, then I look at his mother who is across from me but the closest person to my left. I sigh getting up and get down into the push up position. I didn't feel comfortable saying I would rather text Dallas dirty messages, but it was the truth.

"Its okay Jeffery, you can answer the question. It is just a game." Bryan said smiling at me from the dinner table. I shake my head no and smile as I begin doing pushups. The three of them cheerlead for me and I pump them out.

I stand up, my hand on my hip as I wipe my sweat and catch my breath. Once I finish wiping my sweat I was taken back by Dallas. She was standing in front of me offering me a cold bottle of water.

"Thank you Mrs. Dallas." I say looking down on her and getting a peak of her cleavage. I had a few inches on her and I was able to see right down her button up pajama shirt. From what I could tell it looked like she wasn't wearing a bra.

She smiled looking up to me as she turned around and walked to her seat. As I continued sipping my water, my eyes found her motherly hips swaying. As she walked her loose fitting pajama pants gathered in between her thick thighs and her apple bottom was very pronounced in the silks she was wearing.

I imagined myself gripping her waist, pounding her plump round ass from the back until she submitted. Jesus she was thick and my 18 year old mind was going wild. I finished the bottle of water and made my way to my seat.

"So I take it Jeff would rather talk dirty with Dallas." Bryan said, stuttering his words. He must have been hammered. He may have been on his fourth beer at this point.

"Dad don't say that." Austin said angrily at his dad. In the midst of Austin bickering with his dad, Dallas and I locked eyes and I smiled. She smiled and blushed a little as she finished the rest of her second beer.

Austin flipped over his card and it read, "Would you rather have sex with your mom or dad?" Austin nearly fainted as he put his head down on the table.

"Its just a game son, either answer the question or do 25 push ups." Bryan said trying to give his son some guidance.

Austin eventually got up and struggled his way through the first 15 push ups. The other 10 he simply could not do.

"That's alright son, at least you did more than half of them." His dad said as Austin returned to his seat.

Bryan fished a card out of the stack and read it, "Would you rather have sex in a smelly bathroom or a stain filled bed?" Bryan's face was full of disgust and every one laughed hysterically. He poured himself a shot and drunk it in one gulp. Afterwards he made another face people usually make when drinking alcohol straight.

Dallas drew her card next reading it, "Would you rather give oral or receive oral?" She looked at her husband smiling and continued "I don't think I can handle any more shots. Mmm. Honestly, I'd rather give oral than receive oral." Austin must have had enough because after his mother finished answering the question he got up and stormed upstairs to his room.

Bryan got up following him up the stairs while shouting the same mantra, "Son! It's just a game."

"Maybe, I should've just taken a shot." Dallas said smiling at me.

"No, I loved hearing about your love to give oral." I say coyly back at her. I don't think I stopped smiling since she said she loved giving oral. I couldn't help but imagine palming the back of her head as I stuffed her mouth with my hard penis. I could just imagine what her tonsils felt like.

"I bet you would like that wouldn't you, Jeffery?" Austin's mother said in a seductive tone.

I couldn't believe my ears and I couldn't help but wonder if my ears were deceiving me. Austin's mother, Dallas, was asking me if I would like her sucking my penis. She must've been drunk and out of her wit.

I snapped back to reality realizing time was of the essence and I said, "You want to see if I would enjoy you sucking my penis?"

She purred like a teenager in heat instructing me to meet her in the guest bathroom. She got up and headed to the bathroom before I could even process what she said.

My mind was racing. I snuck half way up the stairs to see if I could hear Austin and his dad talking and sure enough they still were. I could over hear his dad consoling him and that was the green light I needed. I snuck back down the remaining stairs and went to the guest bathroom where I found Austin's mother on her knees in her silk pajamas.

She shut the door behind me and looked up at me with lust in her eyes. I unloosed my basket ball shorts and they fell to the ground. She closed the gap between us walking on her knees. I ran my hands through her dirty blonde hair eager to be inside her mouth as I stood over her. She licked her lips, slowly pulling my boxer briefs down and out came my hard penis as it landed onto her face.

She smiled saying, "Its bigger than I imagined." She took my penis in her left hand and begin stroking it. After a few strokes, with her left hand, she was stroking it with two hands. Her juicy lips kissed the head of my penis just as pre cum began to ooze out of it.

Her plump lips naturally parted as the head of my penis made way through her mouth to find her soft and warm tongue. My head rolled back, I closed my eyes, and naturally I began thrusting into her mouth. It felt as if my penis had found its way home inside her warm and wet mouth.

Her tongue ran circles around my penis as I sighed in relief. She ran my hard penis down the back of her tongue and the head of my penis met her tonsils. I pressed into her tonsils and she didn't even gag. I was impressed.

I continued to feed her my meaty penis as if I were feeding a baby a bottle. Cupping the back of her head, I found myself almost balls deep in her mouth. I could tell she was thoroughly enjoying herself the way she occasionally rubbed her breast. She sucked my penis with enthusiasm and in a passionate way.

I snapped back to reality when she pulled my penis out of her mouth. The cold air hit my penis and I so desperately wanted to be back in her mouth. She licked my shaft up and down, massaging my penis with both of her hands.

"You like how I'm sucking your penis, Jeffery?" She questioned me looking in my eyes deeply. I couldn't even answer her question being stuck in a daze watching her massage my penis.

In the midst of the silence, I heard the wood floor creak outside. It sounded like someone was near the door and my eyes immediately found the door knob. My heart nearly fell through the floor when I realized the door was unlocked. I reached over in an instant and locked the door, not ever moving a foot.

Dallas did not even budge and she began sucking my balls, looking up at me. I felt like my nutsack was melting in her warm mouth. She must have read my mind as she eventually put my penis back in her mouth. I couldn't believe I was literally fucking the mouth of my friend's mother while he was upstairs.

Following my instinct, I tried not to be too loud. I gave Dallas the "be quiet" face while I listened to the silence. I continued fucking her mouth long and slow and we developed the perfect rhythm. Every now and then I could hear her saliva and my penis squishing against the back of her throat.

I could feel her milking my penis and it felt amazing. It surprised me how her mouth would remain so wet, yet I could feel her swallowing all of her spit and my pre cum. I guess I know why her husband was smiling when she read the question about spitting or swallowing. She's definitely a swallower and she drained my penis of its pre cum as if it were nutritional. I smiled looking down on her and even with my penis deep in her mouth I could see her smiling back. She continued twisting my penis into her mouth and had been sucking me for about 20 minutes.

I heard a knock at the door and they jiggled the door knob all in one motion. In that moment, I was so very thankful I had locked the door. Dallas ignored the door and continued sucking my penis. I guess I can say her mouth was full so I answered, "Yeah? I'm in here and I'm almost done. Those pizzas must have ran through me."

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