Adventures with Gwyn: Friday Night


Adventures with Gwyn: Friday Night

I'm glad some of you are enjoying these stories. I'm writing them as they happened, so you'll have to forgive me if it doesn't go as quickly as some of you may want. There is a payoff, and if things go well there will be others to come. Obviously, opportunities for future stories will be limited, given Gwyn's and my situations.

I was distracted all day Friday, to the point that my business partner noticed and asked about it. I explained that I was just tired, and didn't sleep well, which he accepted. Our business does well at times, less well at others, but there's always stress involved. He understands the difficulty of getting to sleep at times. I don't think he would have understood my reasons, though.

Around 2 p. m. , Gwyn called my cell. Normally, having the woman you're trying to get an affair started with calling you on your cell, or at home or whatever, would be cause for concern. But the beauty of this situation is that Gwyn, being my sister, can call just about anytime and it not look suspicious.

"Hey, how's your day going?" she asked.
"Good, but I'm tired as hell.

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   I had a great time this morning, though. " I replied.
"Me too. I'm exhausted, but i have to clean up the house for Barry's son. He'll be her Sunday, and I've got so much to do. "
"You still going to be able to come over tonight?"
"Yes, but with a change of plans. Sherryl's plans to stay at a friend's fell through, so I'm going to have to come back home tonight, instead of staying with you guys. "
"Oh, okay. " I was a little disappointed, but realized that it wouldn't really change anything, as long as we could get together Saturday morning, while Ingrid was at work. "We can hang out, Ingrid probably won't drink so we can bring you home tonight, then maybe tomorrow morning I'll come over and… ahem… help you out. "
"Oh, I bet you'd like to help me out!" Gwyn laughed. "It will depend, though. If Sherryl is here, you'd just be in the way and not much help at all. If Sherryl is gone, then maybe. "

I got the message loud and clear.

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   It would depend on what her daughter did the next morning, whether or not we'd have a chance to get together. I felt conflicted; obviously I was sad because I really wanted to seal this deal quickly, but there was also a small amount of relief. There is no way I could turn down a chance to fuck Gwyn if given the opportunity, but if it was taken out of our hands, then I wouldn't commit the ultimate taboo.

"But you'll still come over Saturday night too, right?" I asked.
"Oh, sure, and I'll be able to spend the night then. Sherryl will definitely be at a friend's tomorrow. "
"Oh, okay. Well, good then. " So, sex was probably not going to happen at all.
"What time do you want me to come over tonight?" She asked.
"Well, why don't we just pick you up," I suggested. "That way you won't have to worry about driving home. We can get you about six, then maybe get some dinner?"
"Sure, that'd be great!"
"It's a plan, then. We'll see you tonight. "
"Love you, big bro!"
"Love you too, little sis.

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So we picked her up at six, went to dinner, then stopped by the liquor store to replenish my depleted stock. Ingrid and Gwyn giggled over the selections, finally picking out a number of different sampler bottles they thought would be good. I also had some cheap beer at home, so we figured we were set.

When we got home, the first thing Ingrid and Gwyn did was open a sample bottle of sour apple liquor, toast each other, then drink them down. I looked at my wife, puzzled, and when she noticed her eyes got big.

"Oh, shit. I forgot!" She laughed.
"What?" asked Gwyn.
"I'm supposed to drive tonight, not drink. " Ingrid almost never drinks if we have to drive somewhere later, so that I can drink and she can drive. I offer to be the DD all the time, but she never accepts.
"It's okay, I didn't really feel like drinking tonight anyway," I said, which was true. My stomach was still in knots.
"Are you sure, honey?" Ingrid asked.
"Absolutely! You two tear it up!"

And they did exactly that.

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   They drank beer and periodically did shots, and I laughed more that night at the two of them than I had in a while. Knowing Ingrid had to get up at five in the morning, I kept looking at the clock, which she noticed.

"Don't worry about the time, honey. I'll be fine in the morning. "
"Okay, but it's ten now, and five tomorrow comes awful early. "
"Oh, did I forget to tell you guys?" Gwyn piped in. "Sherryl texted me a little while ago that she's staying with her friend tonight after all. I could have spent the night, but I don't have my stuff. "
"Well, I haven't been drinking," I said. "If it's okay with Ingrid, I'll drive you home and you can pick up your stuff. Ingrid, you can get the bed ready for Gwyn, or come with us if you want. "
"I'll stay here and clean up a bit. You go, and get back safely. "

That couldn't have worked out better if I'd scripted it. We left the house, and I knew the drive was about 18 minutes one way, and I could explain any additional time as Gwyn being drunk and not being able to get her stuff together.

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   I was nervous as hell. I mean, we'd done stuff already, but not physically together. She wasn't making any moves, and I didn't know if I should. Being the mature adult that I am, I poked her arm.

"Stop hitting me!" she laughed, punching me hard on the arm.
"Ouch!" I exclaimed, laughing. "You're a mean little sister!"
"You're a mean big brother!"

We went on like that for a bit, laughing and having fun. When we got to her house, I followed her around like a lost puppy, hoping to have a chance to touch her or something. She went from room to room gathering the things she'd need for staying with us, talking to me about inane crap the whole time. "Should I bring toothpaste?" "Do you have razors? I'll bring my own. " "I'll need conditioner; do you have any. " I answered on auto-pilot, wondering what her game was.

Finally, she had it all packed, and we walked into the living room, on our way out the door.

"Do you have everything?" I asked.
"I think so.

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   What else?" she answered, turning to me.
"How about a kiss…" before I could finish the request, she was in my arms and all over me.

Her passion and enthusiasm overwhelmed me, and I could have spent hours simply kissing, nothing more. Her plans were different, and she grabbed my hand, which was rubbing her back, and planted it firmly on one fantastic boob. I squeezed it and quickly decided that wasn't enough, and slid my hand under her shirt to cup it through her bra. She reached under and lifted the bra, giving me free access to it. By then my other hand had pushed her shirt up on the other side, and she quickly freed that tit as well. I was kneading them and playing with her nipples, all the while continuing our kiss.

"Oh, goddamned!" I moaned. "These are fucking fantastic tits!"

Her hands started roaming all over me, down my back and butt, then to the front to rub my chest and front of my pants. My hard-on was immediately evident, and she rubbed it a few times before returning to my back. Meanwhile, I'd lifted my shirt so that I could feel her naked tits on my naked skin, and slid my right hand down the front of her shorts. I rubbed her pussy over her underwear, trying to push the crotch aside. I wanted at least a finger inside of her. As we were standing, this was proving difficult, so I brought my hand back up and slid it down inside her panties.

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   She shaves almost completely bare, so I had no trouble getting to her pussy lips. I parted them with my finger, searching for the wetness I knew would be there.

Found it! She was soaking wet, and my finger slid easily into her. I marveled at how tight she was, despite having had a child (she later told me that it's because of Keagle exercises. ) She was writhing in my arms, moaning into my mouth. I wondered how much we could get away with, and for how long. I might be able to explain a few minutes away, but I wanted to spend hours with Gwyn, and I knew I'd let time get away from me if we went any further. I broke our kiss.

"Oh, fuck. We have to go," I said. She pouted and mewled, letting me know she didn't like it. "I know; I want you so bad. But we'll have time tomorrow. "
"I know, you're right. "

So one last kiss, and we got back in the car.

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   On the drive home, I rubbed my hand up and down her leg as she felt my cock through my shorts. I contemplated asking her to give me a blow job on the ride home. I know she would have if I'd asked, but I decided against it, because I didn't want it to be just about pleasing me. For one of the few times in my life, I decided to show patience.

We got back home, and the three of us drank a couple more beers, talked some more, and eventually decided it was time to go to bed. My wife made sure Gwyn was settled in her room, and we retired to ours.

The next chapter to come will tell about Saturday morning. .