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Anything Goes
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Straight Male / 32
I found degrading photos of my friend's mom ... I blackmail her into letting me butt fuck her. She has never been butt fucked before ...
To start off, I guess I was a typical horny teenager. I got into porn by the time I was 15. I'm an only child, with 2 parents who both worked. I had far too much time to myself to get into trouble. I had the occasional girlfriend and started having sex when I was 16, but more often than not, I was always in my room on the computer getting into more and more porn.
I was also 16 when I first came across "i****t" themed porn. It didn't really jump out at me right away. Outside of it being impossible to ignore my mom's big tits, I had never really thought about her that way. After seeing enough of the porn, I started to get into the idea more and definitely started thinking about my mom. Every once in a while I'd go and get some of her panties and jerk off into them, being careful not to get any cum on them. It was shortly after my 17th birthday when one morning my dad angrily approached me, with my mother slowly walking behind him. I was always very careful about deleting my browser history and all that, but somehow I must have forgotten to just once, and that's all it took for my parents to find that I had been looking at/watching the mom/son themed stuff. I was mortified as my dad yelled at me and wound up kicking my ass pretty good. I was already bigger than him at that point, but I wasn't going to hit my dad. Mom was basically silent. I could tell she wasn't happy with him taking it so far. My dad left when he was done with me, and mom came and patted my head and then followed him. That was the end of it, or so I thought. I even stopped looking at the mom/son stuff, out of fear of what would happen if I got caught again.
A year passed. It was a few days after I turned 18. Mom had a day off from work and was there when I got home from my shitty job that I had gotten after I finished high school. We made small talk for a while. Eventually, she got kind of quiet and I asked her "what's wrong?" and she told me "oh nothing. Just thinking. Bills, you know?" I dismissed it as just that.
A few minutes later, still quiet, mom asked me "Andrew... do you still think about it?"
Being clueless, I asked "think about what?"
I was sitting on the couch, as she stood over by the recliner and folded laundry. I looked at her as she paused and quietly said "you know... me. Us."
My mind raced. I knew exactly what she was talking about. And yes, I had very much been thinking about her, us. She's a milf, for lack of a better term. 46 years old at that point. 5'5", long brown hair with gray mixed in. Nice, thick figure. Huge tits. I had always imagined what they must look like out of bra and shirt.
I sat, frozen. I let out with several stutters "what? That? Maybe. Why? I mean... honestly, yes. I'm sorry. Why?"
She said "it's okay, sweetie. I've thought about it, too."
I couldn't believe what I was hearing. I stared into my lap nervously for a bit, before looking over at my beautiful mother, who was staring straight at me. She was blushing and smiling. She asked me "what do you like about it? You know... does the mother/son thing turn you on? Is it me?"
Still nervous as fuck, still sort of stuttering, I told her "well, I guess it's both? I think the idea is hot. And you... look at you. You're hot." If I could do it over I'd have probably told her she was beautiful, or sexy, or something more flattering than "hot", lol. But being 18 and nervous, that's what I blurred out. And lucky for me, she loved it.
"What about you? You've thought about it? What do you like about it?" I asked her.
"It's very naughty. I can't put my finger on it, but I haven't been able to stop wondering what it'd be like. And you're very handsome, Andrew."
By now my imagination was in full swing. The thought of doing anything with my mother was enough to give me a full out erection already. She noticed, as I failed to hide it.
She walked over to me, leaned over, and rubbed my cock through my pants. "Why don't you come with me? Let's stop wondering."
She didn't have to tell me twice. We held hands as we walked to mom and dad's bedroom. She told me to get undressed as she headed into their bathroom and shut the door. I quickly undressed and waited. A few minutes passed, and she opened the bathroom door. There stood my mother, wearing this red piece of lingerie and black high heels. She stood in her best "sexy pose" as I stared at her gorgeous body shown off by the see through top of the lingerie.
I was sitting on the bed as she walked towards me. My heart was pounding. She sat next to me and we started to kiss. Passionately. Only seconds had passed before we leaned back and laid down on the bed, continuing to kiss. I felt her up and down. The girls I had been with before couldn't compare to the curves she has. And the kissing was great.
Soon enough, she got into a different position. I knew what was coming. She paused for a moment, as her hand wrapped around my cock, and then she looked at me and said with a smile "you're much bigger than your father. Just so you know." And then she took my cock in her mouth. At first I laid still as she sucked my cock. A few minutes had passed before I sat up a bit, reached down, and put my hand on the top of her head. I ran my hand through her hair, before pushing down on her head and forcing my cock into her throat. She pulled off and excitedly said "that's it baby, make mommy do what you want." And then she took my cock back in her mouth.
I'm not sure how long it went on like that, with me occasionally pushing down on her head. There were times where I think she was going to pull off for a break, but I kept her head down. When I felt myself getting close, I held her head down and began to fuck her mouth. She made distressed sounds but I was so close, I kept going until I was cumming in her mouth and throat. When I was done and let her up, she coughed and caught her breath, and then swallowed my cum.
She stood up in front of me and asked me "so what do you think we should do now?" with a huge smile on her face. I stood and got very close to her. I slid the straps of her lingerie down to the sides and exposed those gorgeous, huge tits of hers. I played with them for a bit, getting a bit rough at times. I also reached behind her and grabbed her ass for a while, and told her "you're so fucking sexy, mom."
She grabbed my cock and said "so are you, Andrew... son."
I pushed her onto the bed. She slipped off her panties and the heels came off. She spread her legs as I shoved them open further. To this day, I'm not sure that anything can beat the excitement of that first time I shoved my cock inside my mom and she yelled "oh my god baby yes! Take me!" I can picture it like it was yesterday. And, I took her.
I didn't even bother starting slow. I knew I was good to go for a while, having already cum once from the blowjob. I fucked her hard and fast, as she moaned loudly. I was rough and I moved around a lot. Her legs out wide, me leaning onto her and putting my hands on her head to pull her towards me; or her legs up on my shoulders, as I leaned down on her and tried to fuck the life out of my mother. She was enjoying every second of it. At one point during a position change, she started fingering herself with me still inside her. I moved her hand out of the way and started to finger her instead, as I very slowly moved my cock in and ..(continue confession)
