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An incomplete history of my sexual experiences with family members - Part 1
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My name's Joe and as promised, I'll start sharing some stories. I tend to get a bit long-winded and I'm hardly a good writer, so bear with me...
I thought I'd go through the beginnings of the sexual experiences I've had with my various family members, starting chronologically with my oldest sister Natalie.
Nat is a little over two years younger than me, brunette, at the time of the events described here she was a tiny bit overweight (though she got really fit and thin not long after) which had the positive effect of her boobs being real nice and juicy. But naturally she didn't focus on that but more on her belly sticking out too much and stuff like that. She also had some problems with acne and hated her skin. She had real self-esteem issues which I always felt was ridiculous because little imperfections or not, she was (and is) very attractive.
Once, after she told a story about some guy not being interested in her at all, I told her that I thought she was beautiful and that she shouldn't ever let anyone tell her otherwise. From that point, I consciously continued to compliment her and tell her that she was pretty whenever I could. Maybe I'm giving myself too much credit, but I believe that really helped her. Maybe it was something else, I don't know, but she started dressing sexier, going out more and being more confident. She also lost her virginity around that time (unfortunately not to me).
Anyway, jumping ahead a bit, the first time something sexual happened between us was a bit like one of those fantasy writings I see on here sometimes - playing truth or dare. I don't know if young people still do that, but back then there wasn't the wide wealth of entertainment we have now, so we did simple things like getting drunk (and/or high) and playing truth or dare.
I was playing at our house with Nat, three of her girlfriends (I know one was named Joanna - I don't remember the other girl's names) and the boyfriend of one of the girls. I figured, 4 girls to 2 guys were decent odds. I didn't really expect anything to happen with my sister, I think, but I certainly wouldn't have been opposed to it if you asked me beforehand.
Back to the game. After some boring truth rounds (doesn't everybody lie whenever he/she doesn't actually want to tell the truth anyway?) we decided, we'd exclusively play dares from that point. Some of them were stupid, some of them were harmless (I'm sure I kissed one of the girls or something), but eventually Joanna dared the girl whose boyfriend was there, too, to touch my dick. After some discussion, she clarified that I wouldn't have to take it out or anything, she'd just touch me through my pants (they weren't jeans, just something thin and comfortable) and so she did. Boy, did she ever. She basically gave me half a handjob through my pants with her very unhappy boyfriend looking on. She left me with a major hardon and then excused herself to the bathroom. I'd like to think she went to go masturbate, but I have no way of knowing and it's probably just my dirty mind.
Since she wasn't there to dare someone else, her boyfriend took the initiative. He was clearly a bit pissed off and probably wanted to get to me or something, so he dared my sister Natalie to finish the job his girlfriend started and jerk me off. He clarified straight off the bat that he wasn't talking any half-measures - he wanted me to take out my dick and have her jerk it until I came. Nat tried to talk her way out of it by saying that it wasn't just a dare for her, but for me as well.
Quickly, Joanna argued that it was completely within the rules and we'd just both get to dare someone else after. She was a naughty bitch, that one. I could tell that she loved the idea of seeing some sister-on-brother action (I would find out later that Joanna was having sex with her brother - though I'm not sure if that was already happening at that point in time).
So, not wanting to chicken out, Nat knelt down next to me and shyly touched my raging hard-on (still through my pants). I could see that she hated doing this and was embarrassed beyond belief. Her face was bright red and she looked straight into the ground. Her touch felt good. Real good. She barely did anything but already I enjoyed it much, much more than anything the other girl had done. But I couldn't let her do something she so clearly didn't want to do. So I gently pulled her hand away and told the guy "No, we're not doing this. This is too fucked up, okay?"
He called us cowards and said that I just didn't want anything to see my ugly deformed cock. I shot back something about his girlfriend clearly digging my equipment. And his Mom, too. Yeah, I went there. I was young, dumb and drunk... Anyway, in the end he backed down and we all called it a night. I actually believe the guy drove home himself (and his girlfriend, too, I guess), which he really shouldn't have in his state of inebriation. Thankfully nothing happened. Don't drink and drive, people!
Joanna was the last to leave and before she did, she pulled me aside and told me that I should really talk to my sister. I hadn't really noticed, but apparently she was still really upset.
So I went looking for her and found her in her room, lying on her bed, crying. I asked "What's wrong, Nat?"
She didn't answer at first and I figured she was upset about that guy or about the very idea of touching me or something, but after some failed attempts to cheer her up, I finally realized what had really hurt her.
It's not an exact quote, but she said something like "You always tell me I'm pretty, but when it comes down to it, you really think I'm disgusting and don't want me touching you."
Yeah, it was probably less long-winded than that. Hey, it's been a long time - I don't remember the exact verbiage.
I (truthfully) told her that wasn't accurate at all and that I just didn't want her to do something she clearly didn't want to do.
"Well..." she said "...I didn't wanna do it front of the others."
My blood was rushing into a very specific area. "Do you want to... now?"
Nat didn't answer. She just nodded. She looked so fucking cute, nervously biting her lower lip as she reached out. Again, she touched me through my pants first and brought my cock back to a full erection.
I pulled down my pants a bit and took it out. She just stared for a second. "Go ahead!" I encouraged her.
"You really want me to?" she asked.
I laughed "I'm a guy. I'll never ever say no to a handjob."
"Even from your own sister?"
"Look, Nat... I love you as a sister, you know that. But I don't just think about you as my sister, I also... I think you're hot, alright? I do. You're so fucking hot!"
She looked at me incredulously, so I doubled down and told her that I thought about her while jerking off sometimes. I guess she finally believed me and gave me a wicked smile.
She wrapped her right hand around my shaft and started stroking while massaging my balls with her left.
"You know... it's kind of nasty to think about your own sister while... you know..."
I couldn't help but chuckle "It's also kind of nasty to jerk your own brother off, isn't it?"
Nat laughed, too. "Yup. I guess we're both nasty."
She stopped massaging me balls and instead put her left hand down her own skirt, rubbing herself. Watching her do that drove me insane. I moaned or groaned or something in between and I could see on Nat's face that she absolutely loved making me feel this way.
"Your dick feels sooooooo good!" she purred "I'm getting all wet, Joey..."
That was more than I could take. Sperm exploded out of my cock, some of it on Nat's arm and shoulder, most of it on her bed.
"OH MY!!! Wow... you weren't kidding. You really liked that, huh?"
I had trouble catching my breath. "Sorry I came so quick and didn't... didn't warn you."
She gave me another amazing smile. "It's all good. I love that I can have this effect on you."
She laid down on her back while continuing to touch herself. I was mesmerized, even though I couldn't really get a good look at what she did under her skirt.
"Kiss me!" she demanded, so I laid down next to her, looked into her beautiful green eyes and kissed her, carefully at first, then more and more urgently. Passionately. Her breathing got short and heavy, then she pulled away her mouth and made the sexiest noise I had ever heard in my life. She exhaled loud and intensely and moaned softly. Her entire body tensed up and was shaking. Granted, I didn't have a whole lot of experience back then, but I had no idea that women could have orgasms like that.
"Oh, Joey... that was... amazing."
"No kidding..."
I kissed her again.
"I love you, Nat!"
"I love you, too."
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Posted on : Jan 7, 2016
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Add Comment
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Commented on Jan 13, 2016
This is great, would love to hear more stories. One about your daughter maybe?
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Commented on Jan 9, 2016
I thought the writing was fine. No need to apologize for it at all. And yeah, it's a bit more to read, but I felt it was worth it. Thanks for faving my galleries, btw!
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Commented on Jan 7, 2016
Amazing! Tell more!
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