Adventures with Gwyn: New Beginnings


I didn't know I had a younger half-sister until just a few months ago, when Gwyn contacted me via e-mail. She told me how she'd been adopted as a newborn, had found her birth mother when she was 14, and eventually found out who her birth father was. As it happens, that was my father, who not only couldn't keep it in his pants but wasn't even smart enough to wrap it. Gwyn also had a half-brother from her birth mother's side, who is a few years younger than her.

It's natural, I suppose, to be mad at my father for his indiscretions, but I quickly found out just what a joy it is to be around Gwyn and her family. Her husband, Barry, is a nice, down-to-earth sort, and we've already had a few deep conversations. And her daughter, Sherryl, (from a previous marriage) is sweet and innocent.

Gwyn herself is very pretty, about 5'3 with a nice figure even at 40 years old, a beautiful smile, and such a fun disposition that I was able to forgive my father, now many years dead. He made a bad decision, but I truly love the result (and her family. )

When she first contacted me, we spoke through email, phone calls, and eventually Facebook. We both wanted to determine if we were indeed related, and finally agreed to have a DNA test performed. The first time I saw her in person was at the testing facility, and I was immediately smitten with her. I felt a connection that, in truth, convinced me without the DNA test that we were related.

I was concerned, though, because I also felt a level of sexual attraction that was unseemly for someone I was sure (and later was confirmed) was my sister. I'm a rational man, though, and realized that the attraction was there, and understandable, because we hadn't grown up as brother and sister. The inherent weirdness of wanting to bang your own sister was mitigated by that knowledge, and also by knowing that there really was no reason to suspect that she would feel the same way.

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   Still, I jacked off many times thinking about her, and fantasizing about broaching the subject with her, knowing I never really would.

So my wife and I hung out with her and her family; cookouts, beer festivals, dinners at nice sushi restaurants, etc. And for 3 months, that's how it continued. I still wanted her, but not so badly that I couldn't control myself. I did find myself trying to look down her (almost always) low-cut shirts for glimpses of her cleavage, and I would sneakily check out her ass whenever she bent over, but what guy wouldn't, really.

We started chatting on Skype, and I even gave her one of my webcams that I no longer needed, and helped her get it set up. After the initial test run, where my wife and I video chatted with her and her two wiener dogs, we just kept it to chatting. Until last week, that is.

She messaged me as soon as she saw my login to Skype, and we started talking. She was a little lonely because Barry was on his way to pick up his son from a previous marriage to come live with them, and would be gone for 4 days. During this conversation, we determined that she could come stay with us over the weekend and she, my wife and I could hang out and have some fun.

Somehow the conversation turned to sex, with her talking about her's and Barry's experiences. Barry, as it happens, is pretty conservative in bed though you wouldn't know it to look at him. Gwyn complained that she'd once tried sticking her finger in his butt during sex, and that he said he didn't like it but she thought he was lying. It was about this time that I knew she was getting pretty tipsy from the beer she was drinking.

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Deciding to be honest with her, I said (typing) "Actually, I kind of like that. "
"Oh, really?" she asked. "Well, you should know your sister is a freak. "
"Well, that runs in the family," I replied. "Your brother is a freak too. "
"I guess both of you are, then. "
"What do you mean?" I asked.
"Hmm… Maybe I could go two for two," she continued, cryptically. Though, in truth, I thought I had a good idea of what she might be getting at and my heartbeat sped up just a little.

Abruptly, she changed the subject and started talking about innocuous stuff, being a little flirty but not filling in details. Finally, my curiosity got the better of me.

"Hey," I said, "do you mind if I ask you a potentially embarrassing question?"
"No, go ahead. "
"Did you do something with your brother?"
"Yes," she replied.
"Just playing, or all the way?" I asked
"All the way. " My heart definitely started racing at this.

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   I wasn't sure how I felt about this, so I didn't type anything for a minute or two.
"You still there?" she asked.
"Oh, yea, sorry. Just kind of zoned out. Hey, were you a willing participant?" I figured she had been, but thought that, perhaps if this happened some years ago he might have forced her or brow-beaten her into doing something that she didn't want to.
"Oh, definitely!" she shot back.
"Then I'd have to say I'm kind of jealous of your brother," I admitted. "When did this happen?"
"Hmm, last year. "
"How often?"
"Three times. "
"Wow. " That was really all I had left to say at that point. "Was it good?"
"Oh, yes, the sex was great!"
"Had you ever cheated on Barry before?" I asked.
"No, just with him. I think it had something to do with him being my brother. "
"So you mean I have a chance?" I asked, heart really pounding.

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   The whole time we were chatting, my wife was sitting beside me on the couch watching television. I was so scared she would look over and see what we were talking about.
"Maybe, lol" she replied.

I had to excuse myself to go get another beer, and as soon as I stood up I realized I had two problems: a hard-on and legs that were barely holding me up. I finally remembered to breath, which helped with the shaky legs, and I quickly went into the kitchen and was able to get myself back under control. I returned to the couch, and to the conversation.

"I'm back. Hey, do you have your camera connected?"
"No, but I can… hold on. " she replied. After a few minutes, her camera came on and I could see her. I didn't want my wife to know Gwyn's cam was on, so I continued to type, as did Gwyn.
"What now?" she typed.
"Well," I replied, nervous but determined, "I'd sure like to see your boobs. "
"You see them all the time; I've seen you looking down my shirt, lol. "
"Yea, but I want to see them naked.

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"Naked?!" she replied, and her face on the cam matched that reaction. I started getting confused, because I thought this was where we were heading, but now she sounded almost offended.
"Okay," she said, and lifted her shirtand shook her boobs at me. She has fantastic tits, and she knows it.
"Oh, shit, you have fantastic tits. "
"I know. I'm kind of proud of them. And they're real, too. " She lowered her shirt, concerned that her daughter might come into the room.
"Thank you," I said. What else could I say at that point? I still wasn't sure how far this would go, knowing not much more could happen that night, but wondering what the weekend would bring.

It was getting late, and after asking her to show me her boobs again (which she did, though again giving me a little good-natured grief about it) it was time to go to bed. I asked her if she'd be on in the morning, and she said she would be after taking her daughter to school. "Maybe we can video chat again," I suggested. "What for?" she asked.

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   "I dunno. " I really didn't know what else to say. "Lol. We'll see, after Sherryl is at school. "

I went to bed with my wife, but couldn't get to sleep. I kept wondering if that had really happened. I would have fucked the hell out of my wife if she'd been interested, but she had to get up early and fell asleep quickly. I wanted to jackoff, but also wanted to wait until the next morning to see what would happen on the webcam. Thoughts of what might happen over the weekend, especially with my wife having to work Saturday morning, kept me tossing and turning all night.

That's all for now; I don't know what's going to come of all of this, but I'll continue these adventures as they happen, if you're interested. .


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