Fixing Up Annie's Cabin

We continued making out for a good five or ten minutes with her grinding into me and with me exploring her tits, her back and her denim-covered ass. I wasn't sure how much longer I'd be able to last without cumming in my jeans.

We came up for air and Annie said, "this is nice!" I couldn't disagree but couldn't say much more than that since my mind was racing at a million miles an hour thinking about what would come next. Those thoughts were interrupted when Annie got off my lap and snuggled back up next to me.

"Jake let's stop here for tonight. I'm having a wonderful time and from what I was sensing under me, you were too!" she said with a big smile. "But we're both pretty high and this is a very big step for us, not because we haven't done these physical acts before, but because we haven't done them together. I'm pretty sure a clear mind won't change the way we feel, but we owe it to ourselves to be sure. Let's talk this out over coffee in the morning and make sure we're both OK with where this is going.

"Of course you're right Annie, but I'm so worked up, I don't know if I'll get any sleep tonight!"

"Yeah, me too. Luckily, I just put a fresh set of batteries in my trusty old friend, so I think I can handle things on my own for one night. And from the looks of things, you should be able to take care of things alright yourself!" She said as she gently padded my crotch.

We got up, moved the logs around to kill the fire and started to walk back inside. She slipped her arm around my back and we strode inside together. Once inside we put some things away and started turning out the lights.

"At least tonight I won't have to be so careful to keep the noise down like I usually do," she said.

"That's pretty hot Annie, I'm not sure if I'll get any sleep tonight if you do that!"

We were making our way to our individual bedrooms when Annie turned to me and grinned, "well this probably won't help either."

With that she lifted up the front of her sweatshirt and exposed her gorgeous breasts to me. It was just a quick glimpse, but it's like my brain took a digital photo of them for posterity. Her full luscious breasts, with just a slight sag to them. They were capped off by generous, rose-colored areolas.

"I guess I won't be keeping my noise down either1" I joked.

"Good night, Jake, I'll see you in the morning.

"Night Annie, thanks for an amazing evening!"

I was getting ready for bed, wondering what the fuck had just happened. Were my fantasies really coming true or would Annie come to her senses in the morning and say it was all a mistake? As I was brushing my teeth, I knew one thing for sure, my dick would definitely need some attention very soon.

I made my way back to my room and noticed that Annie's door was slightly open. As I passed she said, "have a good night Jake, tomorrow should be a great day." I said goodnight to her too and decided not to shut my door all the way either. I didn't know why, but it seemed like a good idea.

I settled into bed but left the fan in my room turned off -- I really wanted to see if I could hear anything coming from Annie's room. The house was dead quiet and my inkling was soon confirmed when I heard a faint buzzing sound coming from across the hall. Was she really using her vibrator?

Before long I heard some quiet moaning coming from Annie's room and I started stroking my dick listening to her sounds and replaying the view of her tits that she had given me fifteen minutes earlier. This wasn't going to take long; I knew that for sure. She wasn't shaking the rafters, but I could hear that Annie was breathing very hard and must be approaching climax. I heard her exclaim a sharp "oh!" and I was right in sync with her, cumming hard into my hand and onto my stomach.

I must not have been as quiet as I thought because Annie soon said, "alright, let's get some sleep now and save our energy for tomorrow!"

"Yes ma'am," I responded and wondered if I'd ever fall asleep.

Sleep actually came easier than I imagined it would. Must have been the combination of the weed, the excitement and the release, but I actually slept pretty well. I also had some pretty good dreams too. Morning arrived all too quickly, probably because we had stayed up much later than we had been. Though a little groggy, I was eager to get up and start my day.

Eager and anxious to be honest. Would it be weird with Annie now that we were sober and the sun was up? Oh god, this could be such a disaster! So I got up, washed my face, brushed my teeth and got into my grungy work clothes. From the sound of things, Annie was getting ready for the day too, though I was a few minutes ahead of her. I got the coffee started and was scrambling up some eggs for us at the stove when she came up behind me, gave me a nice little hug and kissed my shoulder.

"Good morning stud, how did you sleep?" she asked

I replied, "honestly, better than I thought I would have. You?"

"Me too, the release must have helped us both!" she exclaimed.

She brought the coffee pot over to the table as I was getting ready to serve up the eggs. I was delighted to see that she wasn't wearing her regular work clothes yet, she still had on the tee shirt and running shorts that she probably had slept in. As she was pouring some orange juice into glasses, I could see down the scoop neck of her shirt and view those wonderful tits swinging freely. She looked up and gave me a big smile.

"Can't get enough, can you young man?"

"Busted again," I said, "sorry about that!"

She told me that no apologies were necessary at this point and that it excited her to know that she turned me on. As we sat down, we started talking about the events of the evening before. She asked how I was feeling about things and I actually was feeling a bit awkward talking about it. Sex was nothing that I really talked about, just did, so this all felt a little new to me.

"That's just your youth talking, Jake, and that's alright but we'll need to push through that in order to have an honest conversation. You probably talk about sex a lot more with guys than you do with your girlfriends and that's absolutely normal at your age. But when you're ready for a really great sex life, you'll know that you need to open up."

"OK, I think I'm ready Annie, but I'll probably need a little bit of help until I get more comfortable." I replied.

"Don't worry," she smirked, "you've always been an excellent student!"

As we finished up breakfast, we both agreed that even though we were incredibly horny, the day (and the rest of the summer) could easily get away from us if we were not disciplined about the work we came there to do. We'd work during the daylight hours and at night we would have our fun -- lots of fun! Annie asked me if I needed to take care of anything before we got started outside and I told her I thought it was best to "save it for later."

"I like the way you think, Jake!" she smiled

The work that day involved scraping down the clapboards on the side of the house that we'd soon be repainting. Annie had wisely rented a scaffold for us to work off of which also allowed us to work side-by-side. Luckily there's no lead paint on the clapboards, so we could work without protective gear and masks. That would make the conversations much easier.

We turned on some music, gathered our tools, climbed up on the staging and quickly got to work.

As we started working, Annie mentioned that we hadn't actually talked specifically about last night and whether our clear-headed selves wanted to continue what those two stoned maniacs had started.

"I think I know your answer, but this is just too important for us not to be clear about," she said.

"No, you're right and I agree with that. I'm all in on this and so goddamn excited that I can't think straight." I replied.

"That's music to my ears, Jake! One more thing I'll mention though, if either of us ever feels like this is getting out of hand -- or has regrets, we have to speak up. That's the only way that this will work, agreed?" she asked.

"Definitely, though I have a hard time imagining that will ever happen," I responded.

She gave me a beautiful smile and I noticed that she had not put on her bra after breakfast. With her scraping off the old paint from the siding, her boobs were getting a great workout underneath her tee shirt. The friction was also making her nipples stand out nicely.

"I really like the feeling," she said, reading my mind (or catching my stare), "and it's nice to let these puppies out of their cage every now and then for some exercise!"

I loved how comfortable she was about talking about things like this. We had always communicated pretty openly, but not about things like this obviously. This was really helping me open up as well.

"You know, I've fantasized about being with you for quite a long time," I admitted.

"Yeah, I've had that suspicion, and the feeling is mutual," she confided. "Though it hasn't been going on for me nearly as long -- that would have been downright creepy and illegal!" she laughed. "But over the past year or so, I've really started to take notice of you as a man and wondering what it might be like."

"My only concern is that I'm not really that experienced and I'm afraid of disappointing you," I admitted.

"That's natural but let me say this to you. I could tell from your kiss last night that you have it. In my experience, that's the most important indicator. If someone is a good kisser, and has an open mind, then the sky's the limit. Put away your worries, we're going to have an incredible time. Remember, I'm a licensed teacher."

With that we both broke out in laughter and continued talking about all sorts of things.

"Let me ask you," Annie started, "what do you think is my best attribute?"

I thought about it for a few seconds and said, "well, you're probably going to accuse me of being a brown-noser, but this is the honest truth. It's your brain. You are so smart and warm and witty, there's not an ounce of conceit or condescension in you, but you're extremely confident at the same time. That's the kind of person I'd like to be."

"Well, you're off to a great start because I think I'd describe you in the same way. You've got a very bright road ahead," she said. "But maybe the real question is what is my best physical attribute?"

I didn't take any time to reply to that one, "Annie you're the complete package, but if I had to pick one single attribute, I'd say it's your chest," I smiled.

"Yeah, guys love my tits!" she laughed

"No doubt about it Annie, you have great tits, but I'm not just taking about your boobs. Your shoulders, your beautiful skin with the light freckles you have just above your cleavage. It's all so goddamn sexy!" I explained.

"Wow, most guys don't notice the details. That's really sweet," she said.

"What a relief -- I was worried you'd think I was creepy," I said.

"No Jake, that's where the trust comes in. If you were a guy a hardly knew? Totally creepy! But that's not what we have here. It's actually getting me even more excited for tonight. I don't want to over-hype this, but I think we're going to have a fantastic time."

"Annie, can I admit something to you? I'm really excited about tonight too, but it's also starting to make me nervous. I'm really worried that I'm going to let you down. I have been known to have performance anxiety sometimes!"

"Not to worry, Jake. I have an idea of how we can kick things off that will be a lot of fun but should also take away those concerns."

"Care to share it with me?" I asked.

"Nope, it will be more fun in the moment. Just trust me!" she exclaimed.

I didn't know how I was going to make it through the rest of the day.

In late afternoon, some dark clouds started to roll in and thunderstorms were in the forecast. Never a good idea to be on scaffolding when there's a chance of lightning! We cleaned up outside and brought in our tools just as we started to hear the first distant rumbles of thunder.

"Why don't we go ahead and get showered and have an early dinner? I'm guessing once we get started, we won't want to be interrupting ourselves for anything!" Annie smirked.

I finished showering first and started heating up the ample leftovers from last night's dinner and opened us up a bottle of wine. Annie came out in a plush robe with wet hair and said, "don't worry, I'm not done yet." Not that I really cared, she looked sexy as hell in everything she wore.

Just as I was taking the leftovers out of the microwave there was a loud crash of thunder and then all of our lights went out. Annie had let out a little shriek with the thunder and apologized saying, "that scared the hell out of me, but at least it's giving my heart some practice for beating fast." She joked.

It would be getting dark before long, so Annie lit a bunch of candles and asked me to get a fire going since the temperature was dropping fast with the rain.

"This looks pretty romantic, not a bad thing if you ask me." Annie observed.

I poured the wine and we sat down at the coffee table in front of a nice roaring fire and enjoyed our wine and leftovers, though I was probably rushing through this faster than I normally would have given what would be on the other side of this.

"Care to tell me anything more about what you have planned for us after dinner?" I asked.

"OK, here's the deal. A couple's first time together is so important because it sets the stage for the rest of their time together. If you leave it to chance, you are taking some risks -- and I'm definitely not taking risks with us. We've both been looking forward to this for too long." She explained.

She went on saying, "I've found that if both partners have a really good orgasm their first time together, then it sets the stage for great results after that. You'd be surprised though, because of nervousness or whatever, I've found that it's not that easy for either person their first time together, especially if there's been a buildup beforehand.

"So, my plan is for us to start out doing some mutual masturbation. Take that look off your face -- it will be wonderful and sexy, I promise you. And because you're so young and have a quick recovery, we won't even be 'wasting one' by starting out this way. Do you trust me on this?"

"Of course I do Annie. I'm a little skeptical, but I'm putting myself in your hands." I said.

"Literally!" she exclaimed.

We cleaned up the dishes and Annie excused herself for a few minutes and said we'd hang out in the main room of the cabin so we could enjoy the fireplace. I took the initiative and got things arranged nicely, I moved the coffee table out of the way and put a couple of blankets on the floor and moved some pillows off the couch to create a nice, romantic nest. I threw a couple of more logs on the fire and lit some more candles that were elsewhere in the room. Looked pretty nice. I refilled our wine glasses and placed them on a side table so that we wouldn't end up kicking them accidentally.

Annie came back out and looked gorgeous. She was barefoot -- and bare-legged, wearing only a men's oxford dress shirt. I was guessing that she had nothing on underneath of that by the way her breasts were moving around sensually. She had her hair down which cascaded around her shoulders. She was wearing some larger hoop earrings and had on a gold necklace with a blue stone pendant. The pendant was stunning against her lightly freckled cleavage. She totally nailed it. She was also carrying a small pouch with her and saw the quizzical look on my face.

"Nothing to worry about this here, I just brought my little friend along. He'll help us get off to a great start." She smiled.

"Literally?" I joked.

"Absolutely!" She laughed.

She then came over to me, tossed her package onto the couch and hugged me around the neck bringing me close to her.

"You did a nice job out here," she whispered, "this will work perfectly."

She then brought her lips to mine and we were locked in a hot, soulful kiss. Her tongue immediately was on the attack, letting me know that she had no intention of holding back tonight. She smelled fantastic and lightly moaned as our tongues intertwined.

"Fuck, Annie. This is so hot!" I said breaking the kiss.

"Definitely Jake, and we're not even warmed up yet!" she said.

She went back to kissing me and let her hands run up and down my back, and my butt. She then reached around to the front of me and started undoing my jeans.

"I'm not going to rush things tonight, but there is absolutely no need for these!" she smirked as she deftly removed my pants. She then pulled my tee shirt up over my head leaving me just in my boxers. Those didn't last long either as she slowly pulled them down off my hips until they were down on the floor.

"Not bad at all mister, I like!"

I had never had any girl comment on my dick before and I have to say that I was pleased by her reaction.

She had me sit down on the floor with my back against the couch and she stood above me and opened up a few more buttons on her shirt and then leaned down and gave me a spectacular view of her gently swaying tits. She gave me another kiss and then moved over to a nearby chair and took her vibrator out of its case.

She finished unbuttoning her shirt and gave me a view of not only her fantastic tits, but of her pussy as well for the first time. I was blown away; it was exactly the way that I like them. Hairy, but nicely trimmed, a real woman.

"Seems to me that you like this look. I'm glad that you don't go for the porn star look." She smiled.

"Annie, you are so fucking sexy. I'm not sure how long I'll be able to hold out."

"Well let's get started then!" she said.

She smiled and turned on her vibrator and started slowly moving it around the outside of her pussy. She closed her eyes and smiled as she let the vibrator begin to do its work. I began stroke my cock but was careful not to let myself get too far ahead of her.

"You can come over here is you like," she said in a sultry voice.

I was over there before she finished the sentence. I leaned over and kissed her and she slowly stroked my cock with her free hand while she continued to work on herself with the other. I then moved down and began to stroke her breasts, lifting them slightly and running my thumbs over her thick nipples. She was getting more excited and her nipples hardened and her beautiful areolas expanded.

"Please suck on them Jake."

I happily complied, putting my lips around one of her jutting nipples and swirling my tongue all around it.

"Yes, harder!" She pleaded.

I took the nipple into my mouth and began sucking. She began moaning louder and increased the rhythm of her vibrator, really starting to get into the action. I moved my free hand down to her pussy and held my hand atop hers controlling the vibrator. As I continued to suck her nipple, her moans were turning into soft screams and I could tell that she was close.

"Fuck yes, Jake baby. Ooooh, I'm cumming! I'm cumming!"

And with that I could feel the wave of her first orgasm overtaking her. She screamed and shuddered with an intensity that I had never witnessed before. I was in awe. It was like I had finally been called up to the majors!

As her orgasm subsided, she left the vibrator on, but snuck it underneath of her for safe keeping. She then pulled my face up to hers and gave me a deep, sensuous kiss. She caressed my face with the hand she had been using on herself and I enjoyed the beautiful scent of her musk.

We got up from the chair and moved back over to the blankets by the fire and she had me sit back down.

"Now, where were we?" She smiled.

I was sitting down and she was crouching down next to me. She kissed my again and moved my hand down to my crotch, instructing me to get started. I don't think my cock had ever been so hard and I quickly stated stroking myself. She was kissing me and moaning into my mouth as I continued to jerk myself off. She then positioned herself above me and let her amazing tits hang down onto my face. I grabbed one of her dangling breasts and began sucking on the engorged nipple. She moaned and moved her left hand down to my crotch, meeting my own hand and fondling my balls.