Welcome to another one of my stories! My ex-girlfriend said I should share some of these crazy stories with the world. At the time, I never bothered but now with the pandemic I have a lot more time on my hands, so...enjoy! I have changed the names to protect everyones privacy, but the rest of the story is 90% true and 10% filling in the blanks of minor details that I don't remember.
So, if you have already read the second chapter of "Happy to Help", you know that I had a fun weekend planned in early Fall, 2012. I had rented two adjacent cabins in the mountains not too far from where I lived at the time. The plan was to go alone on Friday with Jenny, a smoking hot red head that I had been dating for a few weeks and then to be joined for a larger group on Saturday. The larger group was basically coming just to enjoy a game of strip blackjack. This story is the first night, when Jenny and I were there by ourselves.
Not gonna lie, the whole idea took some explaining with Jenny and I wasn't totally sure that she was ok with the weekend plans. If you read chapter one of this story, you know that she was certainly a naughty girl but any time you get other girls involved, things get complicated. I told her about the original party with the strip foosball game, and how much fun everyone had. It seemed to help a lot when I explained that Laura and Brynn were a lesbian couple whose interest in me was basically just the novelty of having someone around to watch their escapades and that they felt safe with me. I explained their photography fantasy and I was honest about the blowjob but told her the whole story ("Happy to Help" Chapter one) and she didn't seem to mind too much. I told her that if I were trying to run around on her with Laura or Brynn that I wouldn't have invited her to meet them, and it seemed like she started to understand, and even get a little excited. I knew she was a naughty little exhibitionist and I could tell she was excited for the strip blackjack game. I figured once she actually met Laura and Brynn she would be more comfortable. Also, I told Laura and Brynn that I had a big crush on Jenny and asked if they would talk to her to get her more comfortable and of course they said they would. My fingers were crossed.
We left town for the cabin a little bit after lunch on Friday. Like any city, there would be a lot of traffic if we waited for rush hour and we figured why not take a half day and get a head start on the fun? We had a few stops to make and didn't want to be looking for the cabins in the dark, so I packed up and left about 1pm. At the time, I lived downtown and she was in the 'burbs, so I mapped a course to get Jenny, and then make a few other stops.
I decided to put Jenny's kinky side to the test that weekend. I knew she had a kinky side but we hadn't explored much. The first stop on the trip (after picking up Jenny) was at a sex toy shop! She was all grins as we walked into the shop, and picked out some fun toys for me to either restrain her with, tease her with, or punish her with. I picked out a set of handcuffs, some wrist and ankle cuffs, a blindfold, and a small vibrator. She surprised me by picking out a small butt plug, a leather paddle, and three different kinds of lube. There was something very sexy about walking through the store with a beautiful girl and picking out things I was going to use on her that evening.
Before we get any farther into the BDSM section of this story, I'd like to note that I am pro-consent, a feminist and we had a discussion before we even got to the cabin about her limits, her fetishes, and her desired "safe word". I enjoy role-playing the lighter end the BDSM spectrum (no whips and chains for me), as long as my partner enjoys it. Jenny consented in advance to everything we did (rather enthusiastically, I may add), and she never used her safe word, so it wont be mentioned in the story.
We made one more stop on our way, at a grocery store and liquor store. I figured other people would bring stuff but I wanted to make sure we didn't end up running out of booze or need to plan our entire time at the cabin around finding food. I probably went a little bit overboard but I figured we could bring home whatever we didn't drink. I bought a case of champagne, a handle of rum, a handle of vodka a handle of tequila, and plenty of mixers. "Not being drunk enough" would not be a valid excuse if this weekend wasn't truly epic!
We took somewhat of a scenic route. Even though I was anxious to get into the cabin and do fun things with Jenny, I figured I don't get to take scenic drives into the rural areas outside of town very often either. Jenny enjoyed it too. We would have plenty of time that weekend for sexy shenanigans. About 4pm, we pulled off the highway in the little town where the cabins were. I followed GPS until we got a few miles into the country and then I followed the directions that the owner of the cabins gave me. After another ten minutes or so of driving through the middle of nowhere, we pulled up to the front cabin/office that he apparently lived in to get the keys to the cabins we rented. The cabins looked super nice! The property was huge, and the cabins had plenty of space between them. The dude seemed pretty cool, and was certainly a gracious host. He gave me a map of the hiking trail near the property, some instructions on the cabins, and his cell phone number just in case we needed him for anything.
The road that lead from the front cabin to the rental cabins in the back was a dirt road, about a mile long. I had a gorgeous lady in the passenger seat and a trunk full of booze and sex toys, so obviously I was in a hurry but I drive slowly just in case. Within about ten seconds of getting onto the back road, Jenny started taking off clothes. This was certainly a good sign! She had been wearing shorts, sandals and a tank top. She was down to just her bra and panties before I made it 100 yards down the road. Thankfully there wasn't anyone around so I slowed down a bit and took a look. She reached behind her back and unsnapped her bra, letting her amazing tits spill out. Before I could even get a good look at her nipples beginning to harden, she slipped her tiny little thong over her hips and off. Then she tossed all her clothes in the back seat, just like on our trip into the city in chapter one!
"Much better!" she said, as she finished stripping down.
Come to think of it, she was naked a lot more than she was clothed when she was around me. And of course, I was ok with that!
"That is my favorite outfit of yours." I said, gesturing toward her naked body.
She stuck out of her boobs a little bit, and smiled.
"Well, I'm so glad you like it." she said.
We drove down toward the end of the dirt road. There was about seven or eight cabins on the main part of the road and then two on the end. All of them looked like they had people in them but that didn't seem to discourage Jenny from being naked in the passenger seat. Toward the end of the road there were two cabins next to each other, a little closer together than the others, and at a slightly different angle because of the way the road curved slightly before the dead end. This was perfect!
I pulled the car into the driveway, and turned off the car. This would be interesting. It was one thing for Jenny to have gotten out of the car naked in chapter one when the car was in a dark parking garage where we would have been able to see or hear someone coming from far away. But this was broad daylight, outdoors, with more cabins only about 100-150 feet away. She didn't hesitate.
She got right out of the car, naked, and walked around to the trunk with me. She had brought two bags, and picked up one of them.
"Well, this bag has my overnight things. The other bag has my clothes. I won't be needing my other bag, will I?" she said, in her cutest voice possible.
"Nope!" I said, playing along.
She smiled, and picked up the bag with all the sex toys in it and headed inside. I grabbed the box with all the booze and followed her in. The place was amazing! It was a little bit modest from the front but once you get inside it had an amazing view out the back! And the interior was very rustic and well-decorated. This was going to be fun!
I walked over to Jenny and gave her a kiss, and ran my hands up and down her sides. Her arms had goosebumps on them. I leaned in.
"I'm going to finish bringing in the bags and food. Get settled, get the toys out of their packages and get ready. I'll be back. And no, I'm not going to bring in the bag with your clothes." I whispered in her ear.
"Yes, sir." she said.
I smiled, and went out to get the bags. We had so much booze and food that it took three or four trips to get it all in. Of course, I left Jenny's bag of clothes in the trunk. I unpacked the food and booze, filling up the fridge with champagne and food, when I heard Jenny calling to me from the porch.
"Sir, could you lend me a hand? I appear to be in a bit of a predicament here..." she said.
"Just a minute!" I said back.
I put the last of the food in the fridge, and headed out.
The view was spectacular, in multiple ways. The first way was that the cabin had a view that stretched for miles of trees, hillside dotted with houses in the distance and mountains along the horizon. The second way was naked Jenny's hot little body, all stretched out with her hands way above her head. She had cuffed her hands together, and had the hand cuffs hooked on a light fixture. The handcuffs had a safety release in case you were worried about her safety but really she was quite excited for her predicament.
"Goodness, how did a good little girl like you end up in such a naughty predicament?" I asked, as I put my hand on her hip and ran it up her side.
She shivered at my touch.
"I don't know, sir. I wanted to see how the handcuffs work but I dropped the key." she said, in her best "damsel in distress" voice.
The key was on a table clear across the porch. I walked over and picked it up.
"Oh, you mean this key?" I asked, holding it up so she could see it.
"Yes, sir." she said.
"Oh, ok." I said.
I slipped the key into my pocket.
She smiled at me.
I walked over, and put my hands on her hips. Jenny got the biggest goosebumps when she got excited, and I could tell she was really enjoying her "predicament" here. I ran my hands up her sides, and she let out just a little tiny bit of a moan.
I had figured out the first time we were together that her neck was second only to her nipples and her clit in terms of being sensitive. That was a great place to start. I kept one hand on her hip, and moved my other hand up to her neck. I ran my fingers around the back of her neck, and moved my other hand up to massage her neck. She closed her eyes, and let out a deeper moan. I ran my hands from the back of her neck down to her shoulders, and back to her neck.
"Mmm, you know just how I like it, sir." she said.
I ran my hands all the way up her arms to the cuffs, and pretended like maybe I was going to hit the emergency release, but then instead I ran my hands all the way down her arms, and down to her tits.
She had fantastic tits to begin with, but the way they looked with her hands above her head was really spectacular. Her whole body shivered under my touch, and her nipples were ROCK hard. I cupped her breasts in my hands, and then rolled her nipples between my thumbs and forefingers. She moaned.
"Gosh, if I didn't know any better, I would think that you were enjoying your little predicament here." I said.
"Mmmmm...well, sir...mmmmmm....I'm trying to...oooooh...make the...mmmmm...best of it..." she said, doing her best to get words in between moans.
Her tits were tons of fun to play with, both because they were really great tits and also because of the way her entire body reacted to my touch. She practically melted every time I touched her breasts. She closed her eyes and bit her lip, just a little bit. I kept gently rolling her nipples, and looked down at her feet. Her toes were curling.
