Fixing Up Annie's Cabin Ch. 03

Annie and I were having great fun in our off-hours, and it was surprising how much work on her cabin we were accomplishing during the day. Just three weeks into it, we were ahead of the schedule we had laid out.

It helped that I had gotten good at this kind of thing from the summer jobs I had, but it would be unfair for me to take too much of the credit as Annie was even more skilled herself. Her parents had owned a small contracting company specializing in home construction and improvements, so it was in her DNA.

This meant that Annie not only had some excellent carpentry and construction skills, she also had a shitload of great tools at her disposal. Even having thinned out her parent's tool collection significantly, she still had everything necessary to do the work we had planned.

We had finished all of the prep of the cabin's exterior, including replacing some damaged trim and siding. This week we'd be painting. We knew it could get messy, so we dressed accordingly and were careful in our setup to prevent spills.

Just like last week, our side-by-side work allowed us to converse all day -- and we never seemed to run out of things to talk about. At one point I expressed to Annie that I was curious what ground we'd be breaking next. Almost all of my fantasies had been fulfilled in the last few weeks, though she always had a way of surprising me with her creativity.

She thought for a few seconds and said, "The way I look at it, fantasies aren't static things Jake; they aren't a checklist. They live and grow -- and change -- within you. If you want to fulfill fantasies, you need to accept that it's not possible to fulfill them all, because new ones keep developing. See what I'm saying?"

"I do, and I guess that makes sense. So should I be worried that I'm not replacing my 'accomplished' fantasies with new ones?" I asked.

"It's not linear like that, and there's also a mental exercise to get past some roadblocks to creativity. It's good that you're not close-minded about things. I'm happy to help guide you too if you're up for it. I've hinted at some of my fantasies with you, how about we explore that some more and see what it sparks in you?"

"I'm certainly game for that," I said. "Are you talking about some of the role-play you had mentioned the other night?"

"I definitely am, but I'm also envisioning something I'd like to do before that if you're up for it. You know some of the light ass-play we have started doing? I'd like to push that further with you." She said.

I was alarmed by that suggestion. "Annie, I do trust you, but I'm not all that keen on you shoving things inside of me; that's not my idea of fun!"

Annie burst out laughing. "That's not what I meant, Jake, though I did love that look of shock on your face! I'm not talking about your ass, I'm talking about mine! Would you be up for doing some more of that?"

"My god, Annie, your ass is fantastic, but this is all new to me. If I had been asked this a month ago, I would have said 'no way,' but now it's something that is starting to excite me. There's still a part of me that thinks it's wrong and forbidden, so I need to work through that."

"That's what makes fantasies so exciting, Jake! And the standard disclaimer applies here which I think you already know implicitly. As fantasies get more 'complex', let's say, communication is critical. It's important to make sure that everyone is on the same page. So I'll ask you directly, 'Would you like to have anal sex with me?'"

"Why yes I would, thanks for asking!" I said with some mock formality.

"Oooh, this is good; I can't wait," Annie said enthusiastically.

We took our normal lunch break and hurried into Annie's room. Our afternoon sessions didn't give us enough time to perform anything time-consuming or complex, but we were definitely able to make the most of these quickies.

"So what do you think we should do today, Jake?"

"How about we go a-la-carte? We both pick something we'd like for the other person to do to us?"

"Alright," Annie responded with a wide smile, "I'd like for you to go down on me; you've gotten so damn good at that! How about you?"

"Thanks for the compliment, I aim to please! For my selection, I'd love to titty-fuck you. I've never tried it and always wanted to."

Annie smiled and shimmied her breasts at me and said, "These titties were made for that!"

We embraced in a deep kiss and our hands started roaming over each other's bodies. I caressed Annie's soft back under her tee shirt and ran my hands up and down her supple skin. She took a half step backward, which gave me better access to the front of her. I moved my hands around so that I could fondle her big, sexy tits that I had been admiring all morning.

I touched her erect nipples and Annie kissed me even harder. She had moved her hands down to my crotch and was now rubbing my dick through my shorts. We were both ready to go.

We practically tore off each other's clothes and tumbled into Annie's bed. She positioned me on my back and started going down on my cock which was not part of the plan at all. She saw my quizzical glance and said, "Don't worry, I just love the way you smell down here after you've been outside. A little funky, but not too funky. God it turns me on."

She slithered back up my body, while still holding onto my very erect penis, kissing my abdomen and nipples, before planting a big French kiss on me.

Annie raised up and offered me her nipples, which is how I like to get started with her. She swung her full tits above my face and slowly lowered them down to my lips. She was grinding her pussy against my thigh as I hungrily sucked away on her erect nipples.

This all happened rather quickly since we were on a schedule after all!

Annie moved back down to my crotch and placed her beautiful big tits around my dick. I raised up on the pillows so that I could see the action even better. The sight of her gorgeous, freckled breasts around my cock was intoxicating. The look of lust in her eyes was an added bonus.

She held onto her soft tits and moved them around my shaft for a few minutes, getting me more and more excited. She would occasionally lean down and give my prick a nice lick or suck before putting it back between her amazing tits. After doing this for a while, she came up and reached into the nightstand to pull something out.

"We'll need a little bit of lube to make this work best," she said.

"The benefits of experience!" I thought to myself.

Annie squeezed some of the liquid into her hand and gently massaged it all over my prick -- what a glorious feeling with her slippery hand gliding up and down my cock. Then she took more and rubbed it into her breasts. What a sight that was!

She wrapped her tits back around my cock and started moving me through her cleavage. This felt amazing; the slipperiness totally helped. It was a little like fucking her pussy, but very different too. I was starting to get more worked up and Annie moved onto her back so I could really drive my dick into her cleavage.

She used her forearms to keep her tits together while I pounded through the middle. With her free hands, she was able to pull on and tweak her engorged nipples. This was evidently doing it for her, given how much she was moaning. I was beyond excited myself with the physical stimulation and the wonderful sight of Annie playing with her own tits.

"Ugh, oh yes baby, fuck my titties! This feels so good Jake!" Annie said encouragingly.

"Annie, you are so fucking hot, I'm not going to be able to hold out much longer!"

"Cum in my mouth sweetie, I want to taste you!" she pleaded.

I kept on pumping through her cleavage and could feel the semen rising up from my balls. Just before I climaxed I rose up and she hungrily took my cock into her mouth. She grabbed my ass cheeks to push me in further and eagerly sucked down my entire load.

I had left a little cum on one of her tits, which she happily scooped up with her finger and stuck in her mouth. It seemed that everything she did turned me on.

I could tell that Annie wanted to catch up now. I moved down to her crotch and started kissing her beautiful bush. Annie was worked up already and I could tell from her delicious smell. She grabbed the back of my head and pulled me into her. She was ready to go.

I parted her lips and started licking her pussy as Annie was gyrating under me. I moved up and began to tease her clitoris and she responded enthusiastically.

"Yes Jake, baby, please don't hold back. Suck my clit baby, oh god, yes!"

I was sucking and tonguing her clit and Annie was writhing under me. Her orgasm was coming on quicker than normal and was happy to bring her there.

"Yes, Jake, that's it. Ugh, yes! I'm cumming! I'm cumming!!"

Annie shook as her orgasm overtook her and she rewarded me with even more of her sweet juices. Since this had come on so fast, I thought we'd go for a second one, which would also allow me to start exploring what we had discussed earlier.

As she continued to cum, I took my index finger and moved it in and out of her well-lubricated pussy to gather up her juices.

"Oh god yes, Jake, fuck me, that feels great!"

I continued on for a few moments and pushed Annie's thighs a little higher, took my finger out of her pussy, and spread open her beautiful ass cheeks, revealing her puckered asshole. I took my moistened finger and gently started to probe around her starfish and Annie moaned lustily in response.

"Oh, what a naughty boy! That's it, Jake, go for it!" she said.

Her juices were flowing out of her pussy and dripping down to my finger, which provided even more lubrication. After teasing her entrance for a short time, I could feel it opening up to my finger, which gently slid in.

Her asshole was soft and smooth on the inside. I don't know what I was expecting, but I was so turned on by this. I brought my mouth back down to Annie's clitoris and it was like a bomb had gone off. Annie grabbed my head and forced it down into her as my finger continued to work in and out of her ass.

Annie was writhing, convulsing, and screaming with pleasure as her next orgasm approached, "Oh my god, Jake! Yes, baby, that's it, right there! Oh, oh, Oh, OH YES!"

She continued to moan and buck as the orgasm tore through her. Once it had subsided, I removed my finger and brought my face back up to her to share her juices with her. She kissed me passionately and I returned her kiss equally. We were making out, but I was unsure where to place my hand that had been playing with her ass. I wanted to be careful not to break the mood by putting it in the wrong spot.

It felt like Annie was always in complete sync with me as she turned over, reached onto the nightstand, and pulled out a wet wipe. I hadn't even noticed those there before.

"Here you go sweetie, this will clean up your 'scented candle'!" she laughed.

I laughed too, though I thought there's got to be a better name for it.

After I cleaned up, we kissed some more and we snuggled together for a little bit.

"Thanks for doing that Jake, that felt so fucking good!" Annie said.

"Absolutely my pleasure," I replied. "Now I'm beginning to see what all the fuss is about. I'd definitely like to fuck you back there."

"Oooh, I'm so glad to hear that. You're going to love it -- I know I will!" she told me.

We realized we had chewed up more time than we expected, and hopped out of bed and back into our clothes. We threw together a couple of sandwiches and returned back to work a little later than we had planned, but quite fulfilled.

The conversation meandered as it usually did while we were working when Annie brought up something that caught me by surprise.

"I'd like to invite your parents up here for a weekend before the end of the summer. I know they miss you and you'll be living so far away from them once you start your new job, I'd feel bad hogging all of your time."

"I have no complaints with what you've been doing with my time, Annie!" I laughed. She did too.

"Yes, we're having a great time, and there's more of that in store before and after they visit, but I enjoy their company too and would like them to see what you and I have done with the place here. I know, it does mean a weekend off for 'us' but I think we can both handle that."

She was right, and this was the adult thing to do, AND it was her house, so she could invite whomever she pleased. I came onboard with the plan and we resumed our work on the house.

After we wrapped up work for the day, Annie suggested that we relax for a little while, and plan for a later dinner that night. She didn't say exactly why she wanted to change up the schedule, but I soon caught on. We drank lots of water and chilled on the couch for a half-hour or so. Then Annie came over to me, straddled my lap, and gave me a nice kiss.

"Want to join me in the shower, big fella?" she asked.

"I don't know, I was thinking maybe I'd watch some TV instead," I teased.

"That would be a little more believable if I actually had a TV!" she said, grabbing me by the face and giving me another kiss.

We both hopped up and made our way to her bathroom. I undressed and Annie came over and gently stroked my dick which was already fully erect. She turned around and slithered out of her shorts, showing off her perfect ass.

"There's still time to change your mind!" she said, jokingly.

"Not a fucking chance," I said, "not with that beautiful sight!"

Annie pulled up her tee shirt, exposing her heavy breasts and erect nipples to me, and smiled. She twirled her tee shirt around in her hand and flung it over to me, the show causing her breasts to jiggle wonderfully on her chest. She gave me a quick kiss and pulled me into the hot shower with her.

The shower spray felt fantastic and the company I had in the shower was even better. We kissed a lot, felt each other up -- a lot -- and also washed ourselves while we were at it. I loved running my slippery hands up and down Annie's luscious body, wanting the shower to last forever and at the same time to get on with our other activities.

Annie returned the favor and sensually lathered up my body, bringing me to a heightened state of arousal. When we were just about done, Annie handed me the bar of soap and said, "Why don't you make sure I'm nice and clean back there."

Great idea. I enthusiastically lathered up my hands as Annie turned to the wall and lightly braced herself, sticking her ass out to me. I started by reaching around to her front and lathering up her pussy nice and well. Annie groaned with approval and I re-lathered my hand and moved it around to her gorgeous ass.

She spread her legs slightly as I moved my slick hand past the crack of her ass without any friction. I started rubbing my fingers up and down across her asshole and Annie moaned softly in appreciation. I put the soap down and with my free hand, reached back around and massaged her tits, which were dangling down in this position. We were getting pretty worked up in there and decided that we should end the shower and move into the bedroom.

We finished rinsing ourselves, dried off, and made our way back to Annie's room. We fooled around on her bed for a good 5-10 minutes, stroking, licking, and sucking our various parts, but it was clear this would just be a prelude to the big event.

I had been licking Annie's juicy pussy when she pulled me up to her and gave me another big kiss.

"You ready for this Jake? I think you're going to love it." She smiled.

"Yes, absolutely!" I replied.

As I expected, Annie took control of this lovemaking session given the difference in our experiences with this particular element. She moved me onto my back and offered me one of her nipples as she frequently did, and I happily accepted it, giving it a nice little suck before we moved on.

Annie reached into her nightstand brought out a bottle of lube and moved down towards my prick. Not being able to resist, she took me into her mouth for a couple of sucks before she decided that we were both fully ready. She opened the bottle poured a generous amount of lube into her hand and slowly rubbed the warm, slippery fluid up and down my eager prick. She poured out some more and reached behind to lube up her ass as well. She closed the bottle and tossed it back on the bed and it landed next to her vibrator which I hadn't noticed her take out before.

She grabbed a washcloth that she had left nearby and wiped the lube off of her hands. She maneuvered herself into position until she was over my waiting cock and slowly began to lower herself down. She was such a sight to behold from my vantage point. Seeing her squatting in front of me was incredibly sexy as I got a great view of her tits, pussy, and legs at the same time.

Annie's eyes were partially closed and she had a slight smile as she was anticipating what was coming. I could feel a few drops of her juices trickling out of her pussy as she positioned herself above me. Annie was holding my cock firmly as my sensitive head parted through her cheeks and was just touching her wrinkled asshole.

I laid mostly still, allowing Annie to control the situation for now, though I was able to reach up and caress her tits which made her smile even more. Annie ever so slowly bent her knees as my slippery cock pressed against her anus. Just as I was wondering if it would actually fit inside, Annie's asshole opened up and my prick began its ascent into her delicious tightness.

Annie bit her lip, smiled again, and slowly drew in a breath, moaning in pleasure as she breathed out. She was savoring this moment. Now that I was partially inside, Annie gently began letting herself down further onto my prick until she finally bottomed out. Her sexy grin said it all and I couldn't believe how tight the fit was - and how great that felt.

She placed her hands on my chest and leaned down to give me another sensual kiss. Annie began pulling her hips forward at a very slow pace to commence our wicked lovemaking.

She whispered in my ear, "Oh Jake, it feels so good to have you in my ass! Are you ready baby?"

I grunted some sort of affirmative reply and Annie started moving back and forth on top of me. The lube was doing its job as I felt tightness, but no friction as we moved back and forth. Annie was now moving on top of me at a more normal pace and we were both lost in our individual worlds of pleasure. I loved looking at her swaying tits and the growing lust on her face as she moved back and forth on top of me.

"Let's move this into overdrive!" Annie said as she handed me her vibrator. I immediately knew what she wanted as I turned it on and maneuvered it down to her snatch. "Yeah, that's it Jake, put it right on my clit!"

I did as instructed and she again bent forward which pinned the vibrator between us but also gave me access to her wonderful tits. "Please suck them, baby," she pleaded and I happily accommodated her.

With my prick gliding in and out of her tight, hot asshole, I voraciously sucked on her large, erect nipples. Annie's excitement felt like it would shake the whole house apart.

"Oh, oh, oh! Oh my god Jake, that feels so good, suck my tits and fuck my asshole! Fuck my ass baby, yes, that feels great!"

Her orgasm overtook her as she screamed and shuddered to her climax. The juice from her pussy glided down to my cock, which kept us well-lubricated, allowing our action to continue. She wasn't going to be stopping with just one orgasm and the only limiting factor would be how long I could hold out.

Annie moved slightly on top of me, which brought her mouth back to mine and she kissed me hard again. She kept on imploring me, "Yes, fuck my asshole Jake! Fuck my asshole! That feels so fucking good! Keep going baby, please, YES!!!" she shouted as yet another wave of pleasure overtook her.