In high school senior year back in the eighties, I had a friend whose mom would buy us booze anytime we wanted, as long as we drank it at their house. I could tell from looking at her that she was an old barfly. She still had her looks, but her better days were behind her. His mom would pour herself a big glass of Jack Daniel's hand, Jeff the rest of the bottle, and send us to his room. One night, we decided to sit in the living room and drink with her.
Her name was Lynn, and she looked older than she really was. Shoulder-length brown dyed hair with greying roots. She had a nice figure with ample titties hidden under frumpy clothes and a jiggly ass that shook as she walked. I caught her undoing the top button of her blouse out of the corner of my eye. I pretended not to notice as I finished my drink. I looked at Jeff and asked if he was ready for another, and I saw her do it again. Jeff said to pour him one as he left the room to pee.
Lynn's tits just about poured out of her blouse as she leaned forward to pour us another drink. Lynn raised her eyes to meet mine as I stared down her shirt.
"Do you like what you see?" she asked with a devilish smile.
"Sorry," I muttered.
"Please don't be," she said. "I'm flattered. It's been a while since anyone here checked me out like that. Look, you got my nips all hard."
We heard Jeff start to throw up in the bathroom, and Lynn went to check on him. It was getting late, and I wasn't sure I wanted to be left alone with his mom, so I grabbed my jacket to head home.
Lynn came back into the living room, saying, "Jeff's not used to hard liquor like you are. He's feeling a bit under the weather. Where do you think you're going?" she asked. "I'm definitely not letting you drive home. I'll make you a spot on the couch after I get Jeff to bed."
Lynn returned a few minutes later with a pillow and sheets as well as a pair of Jeff's gym shorts.
"Here you go. Maybe we should call it a night; you boys have school in the morning," she said, turning out the lights as she left.
I went to the bathroom to change, but the gym shorts must have been from when Jeff was in elementary school because they were way too small. My boxers would have to do. I turned out the lamp next to the couch and tried to sleep. The street lights prevented that.
About an hour or so later, I woke to someone sneaking down the stairs. I figured it was the horny old slut, and thought, what the hell. If she wanted to suck my cock, then fine. At my age, I wasn't about to pass up a blow job or a chance at sex.
I pretended to be asleep, and she pretended to believe my pretense, as she fished my dick out the top of my boxers. I could feel her breath on my exposed cock. Then, there was a warm wetness. It was awkward at first, and I figured that it had been a while since she'd sucked a cock too.
After a minute or two, things got better, and after some more sucking, I blew my load without warning. She gagged at the first spurt of cum, but she kept sucking and gulping. When I finished cumming, I rolled toward the back of the couch, turning my back to the room.
I woke early the next morning and left before either of them woke up. I did leave a note saying that I needed to go and change before school. I dreaded running into Jeff the next day and actually skipped out of the one class that we had together. He texted me asking if everything was okay. I replied that everything was fine. I wasn't feeling well, so I went home early. Everything seemed to be fine as the week went on, and he didn't know anything had happened between his mother and me. I figured no harm, no foul.
Later in the week, he asked if I wanted to come over again for the weekend. I went over on Friday night. Lynn had a case of beer and the remaining bottle of Jack Daniels if we wanted it. We drank in the living room with Lynn for most of the evening. Around eleven, Jeff wanted to go to his room and listen to music. We talked about the normal stuff guys our age talk about girls at school, which teachers we thought were hot, normal stuff.
The alcohol definitely affected my judgment because I mentioned that I thought his mom was hot. He hesitated for a minute, weighing what I had said before responding. "Yeah, she is pretty hot, even if she is my mom."
That's when he pulled out a box from under his bed filled with porn mags. Some of them immediately caught my eye. Family Affairs, Incest Stories, Taboo Tales. They were all incest magazines. I started reading some of the stories and couldn't believe how incredibly hot they were. I'd never thought about my sister or my mom in that way, but it opened the door to a whole new point of view. I hated my sister and my home life and couldn't wait until I moved out, but the thought of having sex with them intrigued me.
I admitted that I had a stash of porn of my own, but nothing to the extent of his collection. I asked if he'd be interested in trading some. I paged through one mag that had pages earmarked that was about a mom sucking her son's cock. Around midnight, we had polished off most of the case of beer, and we really felt the effects. I still wasn't drunk enough to agree to Jeff's suggestion of jack-off while reading the magazines.
"I'm wiped out. I'm going to crash," I responded. I was planning on sleeping on the couch again, but Jeff pulled out a sleeping bag for me to sleep in his room. I stripped down to my boxers and crawled into the sleeping bag. I hoped that he would fall asleep and I'd go and return the favor to Lynn from the previous weekend, but Jeff put on a set of headphones and had the music up pretty loud. Regardless of the music, I tried to fall asleep.
As I lay there with my eyes closed, I felt Jeff pull my sleeping bag open. I sat bolt upright, yelling, "What the fuck!"
Just then, the door burst open, and Lynn fell face down into the room with her nightgown pulled up around her waist.
Lynn tried to say that she had heard the commotion and came to see what it was.
"Bullshit," I said. "He just tried to suck my cock, and you were peeking through the keyhole. Is this some game you two play? Get your friends drunk so you can suck cock, and your mom can get off watching?" I looked over at Lynn, who shrank at the rebuke. "Wait, that wasn't you last time. It was him. Jeff, I'm not gay."
"Neither am I. Um, I uh. I like the taste of cum," he admitted.
"So what do you do, let him fuck you and then have him eat you out?"
Lynn blushed as she nodded shyly.
"I'm okay with that," I said, looking at Jeff. "You want to taste my cum, but I'm letting you suck my cock. I have to draw the line somewhere." Looking at Lynn, I said, "How about I fuck you, and he can eat it out of you? How does that sound?"
They both nodded eagerly.
Jeff started to ask something, but I cut him off, knowing what he was going to ask.
"Your mom will suck your cock, and nothing is going inside my ass. Got it."
"Good, now that we have that figured out. Let's go to my room." Lynn pulled her nightgown over her head as she led the way to her room. That luscious ass of hers jiggled and got me hard before we even got to her room.
Lynn sat on the edge of her bed and waved me over with her finger. She pulled down my boxers and grabbed my hard cock as she sank to her knees in front of me. I could feel Jeff's glare burning into me as he watched. I glanced over at him as he licked his lips as he stared at my cock. He may not be gay, but he's definitely BI. I put my hands on Lynn's head and started to fuck her mouth for a minute or two. I pulled my cock out and motioned with my head to Jeff that it was his turn. Lynn looked up at me as she took her son's dick between her lips, sucking its length into the depths of her mouth. Lynn's head bobbed on Jeff's dick as she cupped the base of his shaft. Jeff grabbed a handful of Lynn's hair and groaned.
"Jeff, why don't you climb onto the bed?" I said, helping Lynn off her knees. "Jeff, on your back. Up by the headboard." I pointed to the bed between Jeff's legs. "Lynn, on your knees."
I climbed onto the bed at Lynn's backside, rubbing the head of my cock along her slippery slit. Lynn leaned into me, taking my cock into her cunt.
I grabbed her hips and buried my cock deep into her, and began to pump my meat into her slut hole. Lynn's head cocked back as I hammered my cock into her, making her groan. She lowered her head to her son's cock and began to suck it. From my angle, all I could see was her head bobbing up and down. I started pounding her cunt, making my balls bounce off of her pussy, making her moan.