Adventures with Gwen: Chapter 1 – Thursday night

I lay in bed, head buzzing with the events from earlier, while my wife of 20 years slept beside me. She had sat beside me on the couch earlier while I was Skyping with my sister, but due to her obsession with baseball she’d had no idea that I was looking at my sister’s boobs and making plans for when we could have sex.

Actually, Gwen is my half-sister, and I’d only known her for two months. She’d known about me for a few years, but had only recently gotten the nerve to introduce herself to me, and to explain that (as near as she could tell from the information she’d gotten) that we are siblings. I’d never had any doubt that my father had affairs while he and my mother were married, but you still don’t expect to be told a baby was born of one of those dalliances.

Even at 40, Gwen was great looking by any standards. She took after my father more than I did, but there was still enough of a family resemblance to leave little doubt that she was my sister. We had a DNA test performed anyway, just to be sure, and that was confirmed. Over the next two months, my wife and I grew closer to her and her husband, and I was absolutely thrilled about having a baby sister.

We spoke via email, Facebook chat, and occasionally phone as much as we could. We had 40 years to catch up on! We talked about how our lives had been, and compared notes of having grown up in the same smallish town but almost five years apart. Because she now lived some distance (about a 1.5 hour drive) away we didn’t get very many opportunities to get together, so she got a Skype account and we started chatting there, which was better than the Facebook chat app. And on one of the rare visits my wife and I took to see her and her family, I took a spare video camera I had lying around and installed it on their computer.

And so there we were chatting on Skype on a Thursday night. Her husband was going out of town with his father the next day and would be gone for the weekend, and Gwen and her 15-year old daughter Susan were going to come to town on Friday to move some things to her father-in-laws house. We were going to help them move things around and get settled, then hang out some. They were going to stay Friday night, then after a pool party at the house of a good friend of mine, they would head back sometime Saturday evening, or maybe stay with us. We were both looking forward to getting to talk directly.
At first we were just chatting, and Gwen told me she’d had a few beers already since she wasn’t working the next day. I did have to work, but I was having my normal two beers as well. Gwen started talking about the pool party, and how she was looking forward to seeing me in my trunks. I agreed that it would be good for a laugh, but it could put her off her dinner.

GWEN: Don’t be silly! Seriously, Rob, I think you’re hot and I can’t wait to see you.
ME: Well, thank you, but I’m about 30 lbs too heavy to be much to see.
G: Well, we’re in our 40s, so I don’t think any of us look like models. But I like what I’ve seen of you so far.
M: You’re drop-dead gorgeous, so I’m definitely looking forward to seeing you in a bikini.
G: Too bad I don’t wear bikinis, though. I only wear one piece suits, lol.
M: Aw, that’s a shame. 🙂 Still, I’m looking forward to seeing you, no matter what you wear!
G: Even if I don’t wear anything?
M: … huh?
G: Oh, nothing, I was just kidding, haha.
M: Lol, okay. I’m getting another beer.
G: Me too.

I went and got a beer, thinking about how the conversation was going, and when I returned to the couch I sat so that my wife wouldn’t see the computer screen easily. I didn’t know how things would progress, and maybe it was all in my head, but I just had a feeling that I should casually make my own screen a little more private. Again, Ingrid (my wife) was too drawn into whatever baseball game was on TV, and several she was tracking on her computer, to pay much more than passing attention to anything I was doing.

M: I’m back.
G: Me too 🙂
G: Brother, you don’t know what a strange sister you’ve gotten, lol.
M: Well, don’t feel bad; I’m pretty weird myself. (If you’ve read any of my other stories here, you know I wasn’t just saying that. I am a freak! But as it happens, so is Gwen.)
G: Oh, I don’t think you can come close to me in that regard, haha.
M: Oh, yea? Hit me with your best shot!
G: No, I better not say anything else.
G: But I wonder if I can make it two brothers!

Now one of the things I’d found out almost from the beginning with Gwen was that she had another, younger half-brother on her birth-mother’s side, named Chuck. This was starting to sound more interesting by the minute!

M: I’m sure you could if you tried 🙂 Uh… make what two brothers?
G: Hehe… I’ve probably said too much already.
M: Okay.

We talked a few minutes about some other things, but my mind kept going back to what she’d said, and I couldn’t let it go.

M: Hey, can I ask you a personal question?
G: Okay.
M: Have you… done things with your other brother?
G: ma-aybe ; )
M: Did you have sex with him?
G: Yes

I was stunned. I mean, I figured that was what she was hinting at, but to have her admit it was… well, stunning!

M: And it was consensual, right? I mean, he didn’t force you or anything.
G: Oh, no, I wanted it. I started it, in fact.
M: When was this?
G: Last summer.
M: Wow. Was it good?
G: Yea, it was. We only did it a couple times, though.
M: And nothing since then?
G: No.

At this point I was getting very aroused! I’ve always had a thing for incest, and had fantasized about my two older sisters (Gwen’s too, come to think of it) when I was younger. And, truth be told, I’d started fantasizing about Gwen, but in that “no way it would ever happen” way.

But now I started thinking the reason she was telling me all this, and from what she’d said earlier about wanting to see me in my trunks, that she was wanting to do something with me. I wanted to tread carefully, though, so I wouldn’t fuck it up. I’d need to be subtle, and delicate.

M: So, are you wanting to have sex with me?

God dammit!

G: I don’t know. I’ve thought about it, but I’d have to know you wouldn’t get weird about it.
M: Like it wouldn’t be weird enough as it is, right? Haha
G: Lol! Exactly!
G: What I mean is, could you do something like that and not tell anybody? Could you act normal to me around Ingrid and Barney?

Barney was her husband. Obviously these names have been changed for protection. I’m going to spare more of the conversation, as you’d most likely find it boring. I personally obsessed over almost every word of it in the weeks to follow, but it was 2 years ago, and my memory of every detail has faded somewhat. Suffice it to say that though Gwen didn’t say for sure that we would have sex, we both knew if things lined up properly we might.

During the chat, I mentioned that Ingrid was working a half day Saturday morning, and that I would be able to help her at her father-in-laws house if she needed it. I made it clear what I meant by helping, but she reminded me that Susan was coming with her, and that my help would probably be limited to actual help. I was trying to think of some way I could get her separated from Susan for a few hours, and was starting to think it just wasn’t going to happen.

G: Oh, Susan just told me she doesn’t want to come with me.
M: Yay! Oh… I mean, aw, that’s a shame. We’ll miss her not being here.
G: Oh, ha ha. Don’t go getting any ideas, though, buster. It still might not happen. It depends on if you’re good.
M: I’ve been told I’m excellent!
G: Mmm, I bet you have been. And I bet you are!

Things were starting to shape up!

M: Hey, do you have that webcam still setup?
G: Yea, why?
M: I don’t know, I just thought it would be fun to video chat.
G: uh huh, I bet. Lol. Hold on, let me see if I can get it started.
G: Okay, it’s here and hooked up; how do you start a video chat?
M: Hold on, I’ll invite you.

I performed the incantations and gestures to get the magic of video chat going, and Gwen finally got the right combination of answers on her end, and we were looking at each other. My god, she was so hot, even in just a normal top and jeans.

I had the volume turned down, and told her that I didn’t want to disturb Ingrid, so we should just continue typing.

G: Okay. What now?
M: I’d love to see your boobs.

Fuck. I wasn’t doing well with the whole “subtle” and “gentle” thing.

G: What? Why? I couldn’t do that! (I could see her on the camera, laughing and looking a little embarrassed.)
M: Just a little look.
G: You’ve seen them. I saw you looking down my shirt at your cookout two weeks ago!
M: Oh, you saw that huh? (It was true; every time she bent over I looked down her low-cut shirt. Nothing to see but cleavage and bra, but it was still hot.)
M: Still, that’s not the same.
G: Hold on. (She stood up, and went off camera, then returned.) I had to make sure Susan won’t come in.

And with that, Gwen raised her shirt and bra, and I got a look at a pair of the most magnificent tits I’d seen in my life! They weren’t as big as Ingrid’s, but they were firm, the nipples were the perfect eraser size, and even the areolas were the perfect color to offset them. Wonderful, absolutely perfect. She shook back and forth then bounced up and down, making them jiggle. But they didn’t jiggle a lot.

M: OMG! You’re tits are amazing!
G: I know, I’m proud of them. I love to show them off! (She lowered her shirt, taking that lovely vision from me.)
M: They’re real, too, aren’t they? (They looked too good to be a boob job, but for her age, I just couldn’t believe how great they were.)
G: Of course! 100% natural! 🙂
M: I can’t wait to see them in real life!
G: We’ll see hehe.
M: Well, of course it’s up to you, but I sure hope you’ll give me the chance you gave Chuck.
M: Can I see them again?
G: Sure. (She got up and checked on Susan again, then returned and lifted her shirt. After a few seconds she lowered it again.)
M: Aw, that wasn’t very long, hehe.
G: Long enough, buster! Save some for later 😉
M: Okay, hehe.
G: So… are you “fixed.” If not, you’d have to use a condom; I’m not going to take a chance on getting pregnant!
M: Well, I’m fixed in the sense that I’m sterile. I haven’t had working sperm since the Army, for some reason.
G: Really? Or are you just saying that to keep from wearing a rubber?
M: I’m not fan of rubbers, but I’m no fan of getting anyone pregnant, especially my sister! I wouldn’t lie about that.

I wasn’t, either. Ingrid and I were childless after 19 years of not using birth control. We’d both gotten checked; she was fine, I was shooting blanks.

G: Okay, hehe. Just checking. Chuck isn’t fixed, and that asshole came in me! I was worried for three weeks until my period started!
M: That sucks! But no, I wouldn’t do that.
G: Ok.

We talked a little longer, but it was getting late and we agreed to meet on Skype again in the morning after she took Susan to school.

I didn’t sleep well at all. I kept tossing and turning, thinking about her wonderful tits, and the exhilarating conversation. I was so hard, but I wanted to hold off from masturbating, because I had a feeling the next morning on Skype would be interesting. And I was right!