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The first time I suspected my family was not like every other family was when I was 18. Being a teenage boy, I had all the normal hormones and urges, and I had become fond of masturbating. It wasn’t something my family talked about a lot, and I knew that my older sister on occasion played with herself. But it was certainly not discouraged, and to me it was normal to fondle myself in my pants or even out in the open while we were watching television or sitting outside on the patio. In my family, people just did things like that in the open, and no one ever said anything about it. That was how it had always been, and I had even busted my nut in front of my family before. They obviously took notice and would even smile while I groaned and shot a healthy load of cum all over my stomach, but they never said anything bad about it or acted like it was unusual to do that sort of thing in front of them. I somehow knew better than to do it when other people were around, but around my family I was very casual.
My sister Stephie, who was two years older than me, would usually watch me while I did it, and sometimes my Mom would watch for a bit. It was natural for them I suppose to enjoy seeing a penis, especially one that was erect and shooting cum. Stephie would usually stare right at my dick as I would beat it, jerking my dick up and down, up and down, until I would tense up and spew. Sometimes her neck would flush red, or her hand would drift down her stomach towards her thighs. If we were inside the house, a lot of times we would wear as little clothing as possible. Eventually we had become nudists of sorts. We would never go outside naked, but inside the home we would all strip down to nothing and just lounge around that way. If I was lucky, and Stephie was the only one around while I would be masturbating, she would join me and either sit right next to me or right across from me so we could watch each other. We would make small talk or even just stare silently at the other person while they played with themselves, but we never actually spoke about what we were doing. Again, I never thought anything of this, it was completely normal to me. But I would eventually find out just how special our family was.
When I started dating girls from high school, we would do the usual thing of making out or fondling. I remember vividly the girl who opened my eyes to the abnormality of how my family lived. Her name was Liv, and she was a really hot, skinny girl from my Spanish class. I finally had the guts to ask her out, and it turned out that she had liked me all year. After one date of keeping my hands off of her, we ended up kissing pretty heavily from then on. She would even let me feel her breasts while we did it, though they weren’t nearly as big as the women in my family. My sister Stephie had pretty decent C cups and my Mom had very motherly D’s, despite how slender they both were. Liv was just an A cup, but with her small frame it just made her all the more cute. She would moan so sweetly when I would slide my hand up her shirt and touch her nipples while I sucked on her neck. After a few dates of this, I was ready to move things right along.
Every night after our dates, I would go home and take my clothes off, sit down in front of the television where Stephie would usually be hanging out, and jerk off my throbbing erection until I came in thick heavy spurts all over myself. Stephie would be torn between watching me and the tv. Sometimes she would ask me about my dates, while I masturbated. I enjoyed that, because talking about how we would kiss and touch each other would get me off even faster. And though I didn’t know why quite yet, I found myself unusually aroused when my sister would watch me jack off. To me, it wasn’t uncommon at all, and I didn’t see anything wrong with it. But there was this feeling I had that I would later realize was attraction to my sister. I hadn’t been raised to think that incestuous feelings were wrong, though I knew how other people were generally disgusted by incest. Still, I didn’t equate masturbating in front of my family as the same thing.
I would soon make the mistake of revealing my naivety to Liv, one night when we were out on the patio at my house. It was not quite dark yet, but we were alone out there sitting together. I couldn’t understand why she didn’t want to make out like usual. She said she didn’t want anyone to see us, but I couldn’t figure out why. What difference did it make if my family saw us? I honestly didn’t understand. Finally, when it was obvious that for some reason she just would not respond to my touch, I figured I would take care of myself right then and there. She had seen my penis before, and though she had never fully masturbated me, she had fondled it while we were making out. It didn’t seem like a big deal to me. But when I unzipped my pants and pulled it out, Liv looked shocked.
“What are you doing, Brian?!” she hissed, glancing around frantically as if someone would see us.
“What?” I asked, grabbing my semi-erect dick and pulling at it.
“You can’t do that out here,” she said, though I could tell she was amsterdam shemale aroused seeing my penis. She told me on our last date, after squeezing it and touching it for a good five minutes, that it was the biggest she had ever seen before.
“Why not?” I genuinely didn’t understand what she was worried about. I was completely hard now, and slowly jacking myself.
“Your family could come out here any second!” She seemed truly worried, even ashamed for some reason.
“So what? They see me masturbate all the time.”
That was pretty much the line that changed everything. Liv’s face was a mix of horror and disbelief.
“What the fuck does that mean?” she finally asked.
I stopped beating my meat for a second. “They’re not going to care. What’s the matter?”
Liv didn’t say anything, she just watched me jerking off with her mouth hanging open. Not a minute later, the patio door slid open and my Mom popped her head out.
“Everything okay out here?” she asked.
Liv spun around in terror and stared at my Mom with frightened eyes. Mom frowned, wondering what was wrong, but then she glanced over at me and saw what I was doing. She just smiled and shook her head.
“Brian, that’s rude,” she scolded in a half hearted tone. Then she went back inside.
Liv turned back to me, and had the strangest expression. “Oh my god, I have to go.”
She stood and walked back inside the house.
I went after her, my dick still hanging out of my pants. She was already to the front door by the time I made it over to her. She turned finally to let me talk to her, but when she saw my penis still hanging out, she fumed and ended up slamming the door as she left.
“Way to go, Brian,” Stephie said from the living room, watching what happened.
“Whatever,” I said, and plopped down on the couch next to her.
She eyed my dick, and smiled at me. “Wanna talk about it?”
I sighed, and noticed that my erection came back to life. I grabbed my dick and started masturbating. “Okay, sure.”
That night, I couldn’t sleep. I wasn’t bothered so much by Liv not wanting to talk to me as I was by the confusion I felt. I couldn’t understand why she had been so mad at something so normal. Or at least what I thought was normal. As I was talking about it with Stephie, who had taken her top off while she listened, she didn’t say much. I got the feeling she knew something she wasn’t telling me, but the closer I got to orgasm, the less I began to worry about it. I had a huge orgasm, despite the rejection I had felt from Liv, and even splattered a bit of my copious load on Stephie’s leg. She laughed it off and slipped out of her pants, and we just sat there and finished talking while I wiped my stomach and chest with some tissues.
“You should talk to Mom about it,” she finally said, openly sliding her finger between her pussy lips now that she was free of her jeans. “She’ll make you feel better.”
“Maybe,” I replied, watching her finger herself. I was reluctant to approach Mom about this, but later that night when I couldn’t sleep, I figured I might as well try.
Dad was working out of state for a few days, so Mom was sleeping alone. I crept into her bedroom at about 2am, still naked since I usually slept that way. I could hear her softly breathing, so I carefully slipped under the covers and cuddled up against her. I used to do this all the time when I was younger. When Dad would leave for work, I would sometimes sleep with her. She enjoyed it, and I enjoyed it too since she always slept naked like me. I loved when she would put her arm around me and her big soft breasts would press against my back, or she would roll over and let me press up against her backside, and my erection would nuzzle warmly against her butt. My young urges often got the best of me, and I would sometimes thrust softly against her while she slept. If she was ever awake while I did it, she never let on. After I would work myself up to a throbbing erection, I would move my penis so it was right between her buttocks and literally fuck her cheeks, gently so as not to wake her, until I couldn’t hold back my orgasm anymore. It was the most blissful feeling ever, and in a strange way it made me feel close to her, like we were bonding as mother and son.
I hadn’t slept with her in a few years now, but had often thought about whether she missed that as much as I did. She was laying on her side facing away from me, so I sidled up to her and pressed myself against her body. I put my hand on her hip and pulled her against me, though I wasn’t quite erect. I just wanted to feel her warm body close to mine. My hand drifted up her side and rested just below her breast, and I hugged her tightly. She moaned softly in her sleep, and I felt her ass move against me. She was instinctively trying to feel for my erection, or maybe my Dad’s I guess. I was instantly rock hard when I felt that, and almost like we had never stopped doing this, I found my body moving right into place. My penis was between her buttocks, and my hand groped at her breast before I knew rotterdam shemale what I was doing.
“Mmm,” Mom sighed, stirring a bit. “Brian?”
I was surprised she knew it was me. “I was having trouble sleeping.”
She smiled, her eyes still closed. She was only half awake. “I used to love when you came to sleep with me.”
“I miss doing it.” I thrust my hips forward unintentionally, grinding my hard dick into her ass.
She moaned. “You always used to make such a mess of me.”
Oh my god, I thought. Did she really just say that? So she must have known what I had been doing all those nights. I suppose it was foolish to think she wouldn’t, considering the “mess” I would make.
“I won’t make a mess this time, I promise,” I whispered, a bit embarrassed. Still, it was not the scandalous act in my mind that it probably was to the rest of the world.
“I don’t mind,” she said sleepily. “If you need some relief, I’m always here for you.”
Wow, that was such an arousing statement that I almost came right then and there. I gritted my teeth, feeling the pleasurable tinglings in my balls as they tightened up. I held it back for now, but I was glad to know that she would let me get off with her before I left. I would probably need it.
“I was hoping we could talk, if you’re not too tired,” I said.
Her eyes opened finally. “Sure, honey. What’s the matter?”
“It’s Liv,” I said.
I moved back a bit while Mom turned over to face me. It was rare that we had ever slept facing each other, but at the moment it was very exciting to see her naked like this. She was gorgeous for a woman her age. Her breasts looked amazing, even in the dim moonlight from the window. Her beautiful eyes were looking right into mine, and she showed nothing but motherly concern as she faced me and scooted closer so that our bodies were touching once again. She stroked my face with her fingers, and my penis pressed right against her stomach. I was nearly trembling with arousal, and I knew I was leaking precum onto her. She did absolutely nothing to show that she noticed.
“Is it about earlier?” she said.
I nodded, but I was looking down at her breasts. She moved up just a bit to give me a better view of them, but she stayed on subject.
“It’s partially my fault,” she said, with a sad expression.
I frowned. “What do you mean? How could it be your fault?”
She sighed, and her fingers drifted down from my face to my neck and chest. “I’ve always kept you a bit sheltered. I always loved how close you and I were, and I didn’t want to spoil anything between us.”
“What does that have to do with anything?” I was confused, but partly because my aching erection was twitching against Mom’s stomach.
“Most families aren’t like ours, Brian. They’re not close, they don’t talk to each other, and they certainly don’t do…’things’ with each other like we do. And I didn’t want our family to be like that, I wanted us to be close. Your Dad feels the same way. He grew up in a divided family, and all of his siblings fought with each other and grew up to hate each other. I never had siblings, and my parents were very repressed from the way they grew up. When we got married and I was pregnant with your sister, we decided that we would do our best to raise our children in a loving, open and honest home. I think we’ve done a pretty good job of that.”
“I do too, Mom.” Her fingers trailed down even further from my chest to my stomach, tracing around my belly button.
“But it’s my fault that I didn’t do much to warn you about how other families are.”
I shook my head. “It’s not your fault.”
Her fingers grazed through the trail of hair from my belly button down to my groin, and her fingertips just barely touched the root of my shaft.
“I thought maybe as you got older, you would start to understand other families more. Your sister was quick to pick up on it, and she learned early on that she couldn’t tell anyone about the things we do differently.”
“She never said anything to me about it.” I clenched my teeth as Mom’s fingers drifted down my thigh and moved underneath my balls, her knuckles gently bumping against them.
“Did she leave you frustrated?” Mom asked, referring to Liv. Her eyes reflecting a look of motherly love and worry.
I nodded. I didn’t mention that I unloaded with Stephie right after Liv stormed out. But I was far more aroused and excited now than I had been back then.
To my surprise, Mom leaned forward and kissed me on the lips. It wasn’t a deep kiss, but it was very intense for me. I kissed her back, and when I parted my mouth to snake my tongue out, I found hers already on its way into my mouth. In one giant sensation of sexual pleasure, I thrust myself against her, and her fingers wrapped sensually around my penis and squeezed softly. We kissed somewhat passionately, but I was fully submitting to her now like an obedient child. With her tongue in my mouth and her hand jerking me off gently, I came with such force that it took my breath away. I grunted and groaned into her, weakly thrusting blog shemale my hips forward while she firmly held onto me, milking me of semen and pleasure as I twitched and shook, all the while still kissing me. I whimpered as she pulled her face away finally, but kept my penis in her loving grasp. She slid her thumb under the head of my dick and stimulated me in that sensitive spot, literally coaxing another jet of sperm from my balls. The experience was just as emotional as it was sexual, and I couldn’t have felt more love for my mother.
“Mmm, good boy,” she purred, kissing my forehead. “Does that feel better now?”
I nodded, but my breathing was too ragged to speak. She lightly ran her hand along the length of my shaft, and I looked down to see what a mess I had made of us both. There was cum everywhere, but neither of us cared.
“Don’t worry about Liv,” Mom said, laying on her back but turning her head to smile at me. “I know her parents, and they’re good people. If she says anything to them, and they call to talk to me or your father, we’ll smooth things over.”
We just laid there for a while, Mom gently stroking my slimy erection while I pawed at her breasts. There was something so innocently arousing about the situation, I couldn’t see why anyone would see anything wrong with this.
“Mom?” I asked, after a few minutes.
She had closed her eyes, but opened them again and looked over at me.
“Would it be wrong for us to have sex?” I said boldly. I suppose I shouldn’t have been greedy, but I felt so much love for her that I had to know how far she would allow things to go so I wouldn’t betray her trust. And even though I had just came spectacularly, I was still really horny laying next to her naked while we touched each others’ bodies. And of course, I had never had sex with a woman before.
Mom allowed a smile to creep at the corner of her mouth. “You’re still not satisfied, huh?”
I shrugged, but my hand dropped from her breast and slid down her body past her stomach and towards her crotch. Her reply had told me pretty much everything I needed to know, at least at the moment.
“I just want to be inside of you,” I said. But when my fingers felt her small patch of pubic hair, which she regularly shaved, she stopped me.
She looked at me seriously. “Just hold me. For now.”
I was disappointed, but wasn’t about to protest. I loved her, after all, and would never do anything to hurt her. She rolled into me and we embraced. Her leg wrapped around my hip and pulled me into her. I could feel her nipples poking me, and my penis slid down between her legs to rest against her crotch. When I felt her pubic hair against the top of my shaft, I was surprised that she allowed me so close to her vagina. It was practically mashed against the top of my dick. Mom kissed me again, and then nuzzled her face into my neck. I thought we would just go to sleep like that, but after a few peaceful moments, her hand reached down to grasp my penis.
She smiled. “You’re so big.”
I got hard quickly after hearing her say that. When I was at full mast again, she moved the tip so that it was resting against her pussy lips. I was so shocked I didn’t say or do anything. I let her be in full control. She gently rubbed the tip of my cock against her pussy, moaning as she basically masturbated herself. I could have let her do that all night, but after a few minutes of playing, she split her lips open and began to feed my thick cock into her body. I couldn’t believe this was happening! We were actually having sex, or at least something like it. Mom didn’t have any trouble taking my size, and after a minute of soft thrusting, I was buried all the way inside her pussy.
I surged with love for her, and felt so powerful now. I wanted to grabbed her wrists, throw her back onto the bed, and fuck the shit out of her right then and there. But instead, we held each other tight and just laid there like that. Her vagina clutched at me, her muscles literally milking my cock inside of her. I didn’t move much, just an occasional involuntary thrust as she carefully and methodically worked her pussy on me. But we never left our embrace, and it never became heated. It was a simple, gentle, loving act. Still, the excitement of it all was getting to me.
“I’m going to cum soon,” I said, warning her well ahead of the explosion.
She didn’t say anything, she just kept her face nuzzled into me and worked me over with her pussy. Soon I could hear her breath quicken, and she started making little grunts and noises that told me she was getting off. As I felt her pussy clamp down and quiver in climax, I couldn’t hold back my thrusts as my cock exploded inside of her. The room seemed to be spinning and my vision went blurry. My body was on fire as my penis began firing off endless jets of thick white fluid into my mother’s vagina, filling her up and claiming her body with my seed. She cried out as her pussy submitted to my pounding, accepting everything I could give her. I could feel her meaty lips mashed against my pelvis as I crushed my body against hers, our pubic hair tangling together in a slimy mess of our fluids. She was making so much noise I was sure Stephie would hear us. Her guttural moans were broken by the force of my thrusts, until finally she was an exhausted and sexually dominated animal, curled up in my arms.
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