Fixing Up Annie's Cabin Ch. 02

I don't know how many times I came that night with Annie. Alright, I know exactly how many times I did, but why brag? We eventually got ourselves cleaned up and Annie suggested we go back to our respective bedrooms so we could get some rest since we still had work to do the next day.

I had a difficult time getting to sleep as my mind wanted to replay the events of the evening over and over again. I can't say that I minded, but it was funny how my prick was trying to respond to the mental stimulation, but just didn't have anything left in the tank. I also thought a little about where things would go with Annie and me, but decided that I could easily over-analyze things and that would become clearer as time went on. It felt like Annie was in the lead on this and I was comfortable with that, after all, things were working out great so far.

I got up at the normal time and Annie was already up and doing a little work on her laptop.

"Just had a few emails to respond to that I obviously didn't get to last night!" she laughed. "How'd you sleep big guy?" she said with a smile.

"I was a little restless -- guess I might have been overstimulated," I said.

She laughed at that and said that she had some amazing dreams after she went to bed. "It gave me some ideas of things we could try," she said with a sly grin.

I was glad to hear that she wasn't having any regrets about what we had done already. We chit-chatted about various things and what we needed to accomplish that day. Not much different than the day before, just scraping the old paint off the siding on a different side of the house. We finished our coffee, got the rest of our work gear on, and went outside. In short order, we had moved the staging and were already getting to the work at hand.

"So what did you think of last night? Not a bad lay for an old gal, huh?" she asked.

"I'll say, and I'm not going to take the bait about that 'old' reference!"

"Smart man. Great in the sack too. You're at the top of your class, Jake." She responded.

I was very happy to be complimented by Annie. Her opinion always meant a lot to me, though I had never imagined her commenting on my sexual prowess!

"So you haven't asked me why I had us sleep in our own rooms last night Jake. Aren't you curious?"

"Of course I am, but I didn't want to blurt it out first thing," I responded.

"OK, here's the deal. We're great friends and obviously more than compatible in the bedroom, so one might think that we would have a full-on relationship, but--"

"Uh-oh, is this where you say, 'It's not you, it's me?'" I asked.

She patted my arm and said, "Oh god no, it's totally you, sweetie!" she said, laughing -- which oddly enough helped break the tension.

"You might not remember this," she said, "but when you were maybe six years old, you told me that you wanted to marry me. It was so sweet, but I let you down easy, saying that I was too old for you. It was true then and it's true now, even though some very important circumstances have changed."

She went on. "If you were 35 and I were 50, it might be a different situation since you'd have some important life experience behind you. But you're just out of college and have a lot of new, wonderful things to encounter and I will not interfere with that."

"I get it Annie, but I still think we could manage a relationship."

"You'll just have to trust me on this, Jake. We're going to have a wonderful summer together, I guarantee it. And who knows, maybe we'll be able to manage the occasional hook-up after that depending on our mutual circumstances!"

"I do trust you, Annie, you've always looked out for me and I'm a better person for it, but I still think you're wrong." I grinned.

"I'm OK with that. We'll get to a good place, both of us. I promise you."

We turned to less serious topics and continued to chit-chat away through most of the morning. About 12:30 we decided to take our lunch break which was usually for about an hour. Annie suggested that we could fit in both a meal and a quickie if we both really applied ourselves.

"You know what they say, all work and no play makes Jake a dull boy!" She joked.

"How long have you been holding on to that one?" I teased.

"Maybe a little longer than I'd care to admit." She said in a fake-bashful manner.

I was definitely up for having a nooner with Annie. We were both a little sweaty but not smelly and we agreed that this would be acceptable.

Annie raced me inside and as soon as we had closed the door she flung off her tee shirt. No bra of course, so her sexy tits were immediately out for view. My lord, I won the jackpot. Whatever her conditions were about our hooking up this summer, I'd gladly comply. As long as she was willing to let me have her, I'd be game.

We were both out of the rest of our clothes in a flash.

We shared a passionate kiss, but our time was limited so we quickly broke and had to decide what was next.

"What will it be, ma'am?" I inquired.

"How about a good old-fashioned sixty-nine?" she grinned.

That was absolutely OK with me and we quickly made our way over to her bed. We kissed a little bit more and I asked if I could suck on her titties before we got started.

"I was hoping you would. You have no idea how much that turns me on. It doesn't do it for all the girls, but it really gets my juices flowing."

She rolled me over onto my back, gave me one more kiss, and then raised herself up and swung her gorgeous melons right over my face. I caressed them softly and then brought one of her taut nipples closer to my lips. I kissed and licked her breast and then moved in around the expanding, pebbly areola. I started moving my tongue along the perimeter and Annie reacted positively, encouraging me with her soft moans.

She swung her legs over so that she was straddling my thigh and began to dry hump me while I continued to work on her tits. I took her entire nipple in my mouth and began sucking with increasing intensity. Annie moaned louder and rode my thigh harder; I could feel juices trickling out of her pussy and down into my lap. Annie increased her rhythm and her moans turned into screams as she came unexpectedly soon -- not that I was complaining!

She grabbed my face and kissed me hard, giving me all of her tongue. I reciprocated enthusiastically. She then came up for air and said to me, "Well, I guess it's time to get back to work on the house!"

I laughed and said, "That's right Annie, time for YOU to get busy!"

She gave me that beautiful smile and a quick peck on the lips while she effortlessly swung herself around into a sixty-nine position.

"Damn, what a hard-ass!" she chided me jokingly.

I grabbed her firm ass cheeks and replied, "Yes, I agree!"

"Flattery will get you everywhere, Jake!"

She then lowered her sweet pussy onto my face and started licking my prick at the same time. The sensation of eating her out and getting blown by her at the same time was a bit overwhelming but I persevered. Her musky scent was a bit stronger than last night probably because of the work we had done outside that morning and I found it intoxicating. I started slowly licking her juices around the outside of her lips and she responded by grinding herself into my face.

"ohhh yeah, Jake, that's nice."

She then took control of my prick and began licking up and down its length while continuing to moan from the effects of my ministrations on her. Her pussy juices were flowing all over my face and I was in heaven. I picked up my pace and started gently working on her clit and her moans told me I had hit the right spot.

She had begun sucking me for all she was worth and it was having a predictable effect on me. I was bucking my hips, sending my rigid prick in and out of her expert mouth. We were a tangle of moans and writhing as we both neared climax.

Annie came first with a loud scream and she released more juice into my waiting mouth. As she was cumming, she gently grabbed my balls and coaxed me to my climax as well. As I was cumming in her mouth, I grabbed her ass cheeks and pressed her pussy harder into my face. It nearly suffocated me, but my work also brought her to a very quick bonus orgasm. She finished cleaning me up and, as her climax subsided, swung around so that we were once again facing each other.

She kissed all around my face, enjoying the taste of her cum which she had just drenched me with.

"Wow!" she exclaimed, "you've earned extra credit for your efforts today young man."

"I don't know, Miss Simmons, I think I could still use a little extra help. Is it OK if I stay after school today?"

"OK Jake, that was lame! If we're going to role-play, you'll have to come up with better dialog than that!"

Hmm, I hadn't thought about role-playing, but she put the idea in my mind and that might be something fun to try later on.

We made out for a few more minutes, then got ourselves cleaned up, had some lunch, and returned to work almost on schedule. We could hear the sound of workers at other houses along the water, but I can't imagine any of them were getting as much done as we were!

As we were working, you'd think our conversations would either be about sex or would result in awkward silence as we were thinking about sex. For some strange reason, we were able to toggle in and out of these conversations quite effortlessly. Sure some of it was sexual -- which was a real advancement for me since I had been very uncomfortable talking about it before my experience with Annie. But we spent lots of time talking about other topics like books, food, travel, sports -- you know, the conversations that normal people have sometimes.

But I have to admit, I always liked it when the conversation turned back towards sex. I especially liked this because Annie had a way of casually surprising me with new revelations like they were no big deal. I also liked teasing Annie because, as worldly as she was, she could also be gullible on occasion and what 22-year-old guy could resist having fun with that?

At one point Annie asked me what kind of porn I liked best. I had sort of been waiting for this question because my timing was perfect.

I looked her in the eye and said, "Well Annie, it's good that you're asking that because I have to confess to you that I'm really into scat videos. I hope you're OK with that." I couldn't believe I had said that with a straight face and Annie took it hook, line, and sinker.

The color drained from her face and she said, "Well Jake, I appreciate your honesty there, but I'm not sure how to respond to that since I'm pretty surprised."

If I had let this go on, it would have been embarrassing, but, I couldn't hold back my laughter anyway. When Annie saw me lose it, a wave of relief swept over her entire body.

"I wish you could have seen that expression on your face!" I said, aching with laughter.

She punched my arm and said, "You're such a shithead -- and I'm very relieved to know that's just figurative," She was laughing now too; taking the joke in good stride.

Once we settled back down she asked me how I felt about voyeurism. I told her I was of two minds. First and foremost, I found the idea of it very sexy and titillating. Who hasn't walked down a street at night and hoped you could catch a glimpse of a sexy woman undressing in her bedroom window as you're innocently passing by? At the same time, the reality is that it's just wrong to invade someone's privacy, so it's one of those fantasies that is great in theory but not realistic.

"What if I told you that I've found a solution to that?" she said with a twinkle in her eye.

"I'm VERY interested, I just don't know how you'd accomplish that" I replied.

"That's because you're not using enough imagination," she said. "I have a friend across the water with whom I've set up a fun little peep show game. We will occasionally put on a show for each other -- and I guess for anyone else who may be watching at the same time."

"Well, that seems like fun. I've got to say, your friend is one lucky guy being able to 'spy' on you!" I replied.

"That's very nice of you to say, Jake, but why do you automatically think it's a guy?" she asked.

"My mistake! Whoa, you do this with another woman?" -- she nodded -- "My mind is blown. That's so fucking sexy Annie. I'm getting hard just thinking about it."

"Yeah, it's pretty fucking wild, Jake--and it turns me on too. My friend is a college librarian of all things. Her name is Colleen Murphy, we met a while back and have become good friends."

"Colleen Murphy, huh? So I'm guessing she's what, Italian then?" I joked.

"Ha! She doesn't just have Irish ancestry, she's actually from there. She came to the States when she was a teenager, so she still has her accent. I have to tell you, it's quite sexy. She has a great look too. It may not be exactly what you think of as 'traditional Irish', but I think she'd turn you on as much as she does me."

"So are you telling me this just to get me worked up, or is there more to this?" I asked.

"Well given how nasty you were to convince me you were into shit-porn, my teasing you with that would be fair play wouldn't it?" She chided me.

"OK, OK, I'm sorry. I take it all back! Please tell me there's more to this." I pleaded.

She laughed and patted me on the chest. "Yes, there is. I've been texting with her today telling her about my new boy toy and she'd love for us to have a show tonight. She said she'll strip for us, as long as we'd be willing to leave some light on in my room when we go at it tonight."

I hadn't thought about being part of the show, but I guess that's only fair. Considering it was a friend of Annie's, it felt less lewd than it might have been--and a little lewd is OK with me.

"Sounds like a good deal to me," I said after mulling it over for a few seconds.

"Alright then, let's finish up this afternoon's work, and let's be sure to stay hydrated. We're going to need it for tonight."

We worked on the house a little later than normal since we wouldn't be able to start things with Colleen until the sun went down which would be almost 9:00. Plus tomorrow was Saturday and we usually didn't do much work over the weekends, so we figured it would be best to finish up the scraping today.

We finally wrapped up around 7 and Annie asked me if I'd like to join her in the shower.

"It's purely practical Jake, we must do our part to save water!" She winked.

The cabin didn't have a luxury bathroom by any means, but the shower was big enough for the both of us and this was very nice. We decided that we wouldn't get each other off until the show with Colleen started, but it was a big turn-on being in there with Annie.

We kissed a lot and enjoyed the hot spray and stream of the shower. She let me wash her and it was so sexy being able to run my soapy hands all over her luscious body. Her gorgeous neck, beautiful shoulders, fantastic breasts, taut stomach, tight ass, perfect pussy and slender thighs. Yes, I had run out of adjectives, but not enthusiasm.

I played with her tits and pussy a bit and enjoyed soaping up her ass cheeks a little more than I expected to. As agreed, I didn't try to get her off, though it was tempting.

We had another deep kiss before she got to work on me. She was talking dirty while she was cleaning me, telling me all the things she was planning to do to me this weekend. It was a long list, but Annie is nothing if not diligent so I was happily confident that she'd succeed.

She spent a little extra time on my dick which felt wonderful, but, again, did not try to get me off. She also spent a little more time soaping up my ass cheeks and I enjoyed that too a little more than I would have expected.

We eventually rinsed off, shut off the shower, and dried each other off. It was still only 7:45 so we had time to make a nice dinner and open a bottle of wine before the festivities with Colleen would kick off around 9:00. The excitement was building!

By the time we had finished dinner and cleaned up the kitchen, it was getting pretty close to the appointed hour. I was wondering what kind of view I could get of Colleen since her house was across the water, did Annie have a pair of binoculars she used for this? That could be a bit cumbersome especially if you wanted to have a hand free.

Annie took me into her bedroom and I noticed for the first time that she had a telescope near her window.

"Has that always been there?" I asked.

"Yep, I guess you never paid attention to it with all the other distractions in here." She smiled.

Annie pulled a stool over which was the perfect height for the way the telescope was situated and turned off the bedroom lights so that we could see outside better.

"Ready Jake? I think you're going to like Colleen," she said.

"Weirdly nervous," I replied, "now you're sure Colleen is completely on board with this? She knows I'm with you?"

"Don't worry," she said.

I looked through the eyepiece of the telescope and could see what looked like a spare room in the house across the water that had been turned into an office. There was no one in there and the light was pretty dim. I felt a little disappointed and wondered if they had gotten their signals crossed.

"Patience, young man," Annie said.

A moment later the light came on and an attractive woman came in and sat down at the desk. She opened her laptop and began working on it. Hmm.

Since I was the one looking through the telescope, Annie asked me to describe to her what I was seeing so that she wouldn't be left out. I happily complied even though my mouth was a little dry with anticipation.

The woman worked away for a little while and I took notice of her features while she did. She had gray hair pulled tightly into a bun, though she did not look all that old. Her face had a few laugh lines and crow's feet, but other than that was quite youthful. She wore a pair of oversized black glasses which did a great job of convincing me that she was a librarian in real life. She had a wide, sexy mouth that had formed into a slight smile. She didn't appear to be wearing much makeup, maybe a little mascara. However her lips were painted in a deep red -- something you don't usually see on a librarian, at least not the ones at my school!

The woman then looked up and out the window towards Annie's house and her tight smile broadened just a bit. She turned around her laptop so that her screen was facing outward.

"She has a document on the screen and has typed in large letters, 'Hi Jake, it's nice to meet you!"

"See, I told you not to worry!" Annie laughed.

Colleen then closed her laptop, giving me a better view of her. She folded her arms on the desk in front of her and seemed temporarily lost in thought. She parted her dark red lips slightly and brought her tongue up to her teeth, which I took to mean she was thinking up something devious. Boy, she knew what she was doing. She hadn't even shown me the slightest bit of skin yet and I was already fully aroused.

I continued describing the scene to Annie and she asked me what Colleen was wearing.

"It looks to me like a pretty simple blouse, maybe silk? It buttons down the front and the two top buttons are undone, which looks pretty normal. She's wearing a nice strand of pearls and it looks like pearl earrings too. Before she sat down, I think I saw that she had on a long black skirt and maybe some black stockings too. She was wearing nice shoes, not too big of a heel but she looks pretty tall to begin with, so that's probably why."

"Very good attention to detail, Jake," Annie commented.

"Yeah, she is definitely making an impression on me."

Colleen then slowly got up from the desk and turned and walked away from the window. I couldn't tell much about her chest in that blouse but admired the nice lines she had in her skirt as she walked away. Then the lights suddenly went out in the room.