Ski Cabin Surprise

Basics first I guess, I'm Mark, had my 26th birthday a month and a bit ago and love pretty much anything outdoors. I don't hit the gym but do exercise at home and am reasonably fit with curly black hair and dark eyes. I'd been dating Emma for just over a year and we'd recently decided that when the lease on her apartment came up for renewal that she'd move in with me and when mine expired later that year, we would decide whether we were going to renew it or find another place together. Emma was almost model material, long/well shaped legs, tight/firm ass, long/wavy black hair, well built with firm 34 D tits and a gorgeous smile. Why do I saw 'almost' model material? Well, unfortunately when she was younger, she was bit by the neighbour's dog and it left a noticeable scar down one side of her face but that didn't both me because I'd fallen in love with the person, not the looks but she was very sensitive about it. When we first started dating, she did everything she could with makeup to hide it but once she realized that I was comfortable with it and it didn't affect our relationship, she gradually quit hiding it.

Like most younger couples, there were lots of things we wanted to do together but as my dad would have said, we had champagne tastes on a beer budget. Both of us had full time jobs but between rent, food, insurance, gas and car maintenance, neither of us had much money left at the end of the month. We both loved downhill skiing and one of the things we wanted to do since we'd met was to rent a cabin for a few days, ski and have a bit of a vacation. Reality was that we'd have a hard time even affording a hotel room near a ski resort, so a cabin was pretty much out of range. We'd talked about it a few times and tried to think of another couple we could maybe ask to join us to reduce the cost but we couldn't think of any who enjoyed skiing that we'd want to share a cabin with. It was mid-January and we were back to trying to figure out if there's a way we could make our skiing trip work when suddenly Emma said, "Hey, how about Jade and Chris?"

Jade was her sister, younger by a couple of years and Chris was her recent boyfriend. As hot as Emma usually looked, Jade was somewhat plain looking. I had no real idea how she was built because she always wore baggy sweatpants and either an equally baggy sweatshirt or something similar. She kept her dark hair cut short, didn't use much makeup and had just recently gone to contacts and gotten rid of the glasses she'd worn most of her life. If I had to pick someone who wouldn't be likely to want to spend a weekend at a cabin, it would be Jade. She loved video games, going out to restaurants, bars, dancing but I'd never seen her do anything outside other than go from inside to a car or back.

"Jade? Unless she's totally changed in the last few days, she wouldn't go to a cabin in the woods even if you paid her."

"Well, that's what I thought too but she's really in to Chris and he loves hiking and skiing as much as we do. He's been trying to convince her to go away for a weekend and try skiing but she doesn't want to do it because she thinks she'll be bored or not like it. Maybe if we shared a cabin, she'd go and that way we could afford it by only paying half."

I was 99% sure she'd say no but I knew that when Emma gets an idea, it's better to let her run with it until she realizes it won't work so I said, "Why not, give her a call and see what she says."

I could hear her and Jade on the phone as I kept doing what I'd been doing and was totally surprised to eventually hear, "That's awesome, we'll find some options and let you know."

Long story short, Jade decided to at least give it a try to keep Chris happy and we had our other couple to split the cabin with. I figured I'd best get things booked before she changed her mind and we'd soon secured a nice little cabin, not too far from the resort that had a living room with a big fireplace in the middle along with the kitchen and a dining area with bedrooms at each end so hopefully, both couples would be able to have some fun in the evenings as well. It was pricey but split 2 ways, it was actually a better deal than a hotel room just for us.

Of course, as with most things, nothing ever seems to go totally as planned. The first problem was that Emma's period started early so she was about two days into it before we left and I knew that meant she wouldn't be interested in any sort of sex for at least a few more days. Oh well, we'd still be able to enjoy the skiiing and the cabin so it wasn't that bad. When we got there, the cabin was awesome and so was the resort. The second problem came during the last run of the first day. Another skier lost control and cut in front of me, causing me to wipe out and gave my ankle a nasty twist. I was pretty sure it wasn't broken but I knew that I wouldn't be skiing at least the next morning and likely not all day.

We did breakfast the next day and the three of them headed out to the slopes. I'm sure almost everyone has gotten caught doing something they'd have been much happier not to and been able to talk their way out of and a lot of people have gotten caught doing something where there was no way out rather than just own it and hope for the best. That was me just before noon the next day. I was laying on the couch, naked, sliding just over 7" of nicely ribbed vibrator in and out of my ass when the cabin door opened. Hoping it was Emma, I looked back just in time to see Jade staring at what I was doing with her mouth hanging partly open. Fuck! No way out of this one so as calmly as possible, I pulled the toy from my ass and asked, "So, what brings you back early?"

She burst out laughing at my question which certainly helped cut the tension. "I made it through yesterday and tried it again today but I really don't like skiing so I thought I'd come back and have a drink or two. Looks like I interrupted your fun though. I have to ask, would you have sooner it was Chris that came back, I don't think he'd be interested but...."

I cut her off there with a "hell no! I enjoy a bit of ass play but don't want any sexual contact with a guy, a bit of ass play with a toy just feels good."

She was still staring and I quickly realized that while I'd pulled the toy out, I hadn't pulled anything over me and she was still staring at my lubed ass and mostly hard cock. When I reached for a blanket, she just grinned and said, "A little late for that don't you think? Besides, it looked kinda hot, does it turn Emma on when you do that with her?"

"Well, she thinks it's weird for a guy to enjoy anything anal and she's not interested so I only do it when she's not around."

I'd always thought that was odd because while we didn't do it regularly, whenever it was my cock in Emma's ass, she always enjoyed it but no amount of logic would convince her that if my cock in her ass was ok and felt good then there should be nothing wrong with her using a toy on my ass because it felt good. Oh well!

"Too bad for her, I always thought she was a little too strait-laced sex wise. Hell, I'd blown three or four guys before she even gave one a hand job."

That got a smile from me thinking that Emma certainly wasn't the most sexually adventurous girlfriend I'd ever had. My thoughts were interrupted by Jade saying, "So I guess that means she's never actually used a toy on your ass either? What made you decide to do it today?"

"Well, I'd watched a bit of tv, had a shower, was resting with some ice on my ankle and on my third drink or so. Emma's period started early so I'm not getting anything more than a kiss for a few days so I'm super horny and even though your bedroom is at the other end, you're loud enough that I could still here the two of you last night."

That got a bit of a blush from Jade before she said, "Ya, we were both a little hornier than usual and he gave me a good fucking bent over the end of the bed."

Until this trip, I'd certainly assumed that her and Chris were having sex but was totally surprised by how open she was about talking about it. Next was the inevitable question to her of, "So, I'm really hoping that you won't tell Emma or Chris about this."

"Don't worry, if I'd been laying there fucking my ass with a toy, I'd hope that you wouldn't say anything either so you don't need to worry about that."

At the thought of watching her using a toy in her ass, my cock did a bit of a jump and got slightly harder which wasn't missed by Jade. After a second or two of quiet, Jade looked at me and said, "I never thought I'd be saying this to you but you're obviously still aroused and were enjoying fucking your ass with that vibrator and seeing it got me a little turned on too. Would you be open to me watching while you finish what you started or maybe even let me finish what you started? Chris is a bit like Emma, good in bed but not really 'adventurous' and I know he'd never even let me finger his ass so using a toy on him would be totally out of the question even though I love it when he shoves his cock in my ass and considering how often he wants to do it, I'm pretty sure he enjoys it too!"

When she suggested watching, my cock gave a couple more good twitches, when she said she'd be open to using it on me, my cock started to reharden and by the time I'd processed the visual of her taking a cock in her ass, I was fully hard again. "Having you watch would be great but if you want to actually be the one doing it then that would be awesome."

"Ok, but you're not fucking my pussy or ass, those are just for Chris and no touching either."

I noticed she hadn't said anything about her mouth but figured I'd keep quiet about that for now. "Would you at least undress, you've seen me naked so it would kind of be fair."

Jade considered that for a few seconds before saying, "That'd be fine" and without any hesitation, she started stripping off her clothes.

I'd never pictured her as big-breasted and I quickly realized why. Once her outer and inner layers hit the floor, her tits were held in place by a very snug sports bra. When she pulled that off, what had looked like a B or maybe smallish C-cup tits quickly became at least D and possibly DD and her nipples were already wonderfully hard. Next came the snow pants, pants, long johns and finally her thong. Even though I wasn't going to be allowed to touch her, the sight of her bare pussy with the lips parted just enough that I could see her clit poking out between them was a beautiful view and I told her so.

After a quick, "Thank you!" she held out her hand and after a second or two of confusion, I realized what she wanted and handed her the vibrator. With a grin, she moved around the couch and guided one of my legs to the floor and the other up over the back of the couch, giving her an easy view of my ass. Even though I'd already been playing with it, I was a little concerned that she might be too rough but as she eased it into me the first time, I quickly found that she was slow and gentle with it and watched in interest as it slid it out and then back into my ass.

"How am I doing? Does it feel good?"

Seeing as my cock was fully hard and throbbing with each thrust, I really didn't need to answer but I said, "Feels damn good, even better than when I'm doing it myself."

"Then just lay back and enjoy!" and with that, she started going a little harder and a little faster.

To my surprise and pleasure, a few minutes later she reached over and started tentatively stroking my cock. That increased my moaning which made her smile, nod and stroke me even faster. I'd been playing for bit before she came into the cabin and now that I was finally getting my fantasy of a woman using a toy on my ass, I knew it wasn't going to be long before I came. When I finally felt the tingle that told me an orgasm was on the way, I told her I was going to cum. I was hoping that she'd at least keep fucking my ass and stroking my cock while I came so I was totally surprised when she suddenly shifted and instead of her hand stroking the length of my cock, she took my cock into her mouth, got a nice seal with her lips and firmly sucked on it as her head bobbed up and down. That was all it took and with an even louder moan, I started cumming. I usually have a fairly big load and the more excited I am, the bigger it is. Apparently, I was really excited today because before she could swallow it all, there was some oozing from both corners of her mouth but she didn't stop sucking until my cock was softening.

That's when she eased the toy out of my ass and after wiping up the dribbles with a finger and licking it off, she asked, "Was having a woman do it as exciting as you'd hoped?"

"Definitely! I just wish that your sister would be interested in doing it."

"Well, you're not the only one that enjoyed it and if you're awake later, you're going to hear Chris and I having one hell of a hot session in the bedroom because I'm super horny and really wet from what we just did. Who knows, if Chris and Emma aren't into this kind of thing then maybe you and I can do it again sometime."

That was a very interesting thought and by the time the other two got back to the cabin, everything was cleaned up, supper was almost ready and we were sitting watching a movie on the TV. True to her word, that night both Emma and I could clearly hear Jade and Chris having sex and to my total surprise, Emma reached over, stroked my cock a few times until it was hard and then whispered, "I know I'm not usually into sex during my cycle but hearing them got me really turned on, are you interested in some anal tonight?"

It didn't take me long to say yes and I wouldn't have been surprised if Jade and Chris heard us all the way to their end of the cabin. She grabbed the lube, got up on her hands and knees, then after getting her warmed up with a slick finger, I replaced it with my hard cock. If I hadn't cum earlier, I wouldn't have lasted more than a few minutes but as it was, I made it to almost 15 before cumming in her ass but between my cock in her ass and her fingering her own pussy, she'd already cum twice and both of them were loud. My ankle was feeling better the next morning and it was our last day so I decided to try some skiing. Each run hurt more than the one before so just after lunch, I decided to call it a day and head back to the cabin with Chris and Emma saying they'd be back later. Jade had still been in bed when the three of us left that morning and she'd said the night before that she'd likely go into town and do some shopping which was something she definitely enjoyed. I grabbed the shuttle from the resort to where the cabins were and figured if Jade was out then maybe I'd get a bit of a chance to play again, this time without getting caught. When I got to the cabin, I found it wasn't locked so I figured that Jade was still there, damn - there went my chance of a good cum in the afternoon. When I got inside, I couldn't see her but judging from the moaning from their end of the cabin, she'd had the same idea that I'd had. At first I thought I'd do the 'right thing' and just head to our bedroom and give her some privacy but the voyeur in me directed me the other way and through the partly open bedroom door, I could see her laying naked on the bed. I didn't have the best viewing angle but it was obvious that she was enjoying the feel of her own vibrator as she used the other hand to play with her nipples. I watched for a few minutes and was just going to go back to the other bedroom when I heard her moan, "Damn that feels good in my ass."

Hearing that, all thoughts of leaving vanished and I found myself slowly easing the door open for a better look. Unfortunately, there was enough of a creak in the door that she looked around and saw me standing there. I'll give her credit, she didn't scream but she did yell, "What the fuck are you doing there?"

"Well, other than the obvious of listening and watching you filling your ass with that toy and getting really hard at the same time, not doing too much else. My ankle was hurting again so I figured I'd call it a day and come back here and maybe have some fun. Apparently, you had the same idea."

Slightly calmer she said, "At least I wasn't in the main room and I shut the door for privacy."

"Well, you weren't in the main room but the door was partly open so I decided to look in. I guess I'd best let you finish."

As I turned away, Jade quietly said, "Well, I guess you could watch or maybe help a little."

That sounded quite interesting so I gently asked, "Help how?"

"Well, if you take over with the toy, I could focus on my clit and nipples."

I did and she did, which meant it wasn't long before her moans were getting louder and closer together as I slid the vibrator in and out of her slick ass. As she started cumming, I thought of what she'd done the day before and pushing her hand out of the way, I slid a couple of my fingers into her pussy then fastened my lips over her clit. As I sucked, I also flicked the tip of my tongue back and forth across the exposed tip of her clit. After a few small tremors, her orgasm hit like an earthquake with her shaking, bucking and moaning as she came. When she finally relaxed, she looked at me and said, "Damn, that was amazing. At first, I was pissed you'd been watching but after that, I'm really glad you decided to peep at me."

The same as the night before, supper was ready when the other two got there and as far as I could tell, neither Chris nor Emma suspected anything wrong had gone on. Seeing as we wouldn't have any time to ski before leaving the next day, we had a few more drinks than usual and around 11pm, Emma whispered in my ear, "Guess what? My period's finished so I'm going to take a shower to make sure I'm nice and clean if you want, we can have some fun in bed after that."

A quick kiss sealed that offer and shortly after she got out of the shower, it was Jade and Chris's turn to listen to us have some hot sex. I was already in bed when Emma finished in the shower and I was expecting a hot make out session with lots of kissing and touching but instead, Emma went straight for my cock with her hands and mouth, sucking me until I was totally hard before turning around so I could lick her pussy at the same time. Over the next 15 or 20 minutes, we both enjoyed what the other was doing. Emma came several times and had managed to stop sucking every time I got close to cumming to make it last longer. Eventually, she lifted her head up long enough to say, "If I keep going, will you be able to get hard again tonight for more sex?"

Thankfully, getting hard a second time was well within the norm, so I gave her as much of a "Mmmm hmmm" as I could with her pussy on my face and before long, my cock felt like it was exploding in her mouth. After a couple of quick swallows, Emma said, "As soon as you get hard again, I want to feel your cock going in and out of my pussy until you fill it with cum just like you did with my mouth."

She seldom got into any 'dirty talk' so when she did, I knew she was really horny. "Maybe if you put on a nice show for me, I'd get hard faster."

I'd always enjoyed watching a woman masturbate and Emma knew it too so she just grinned and grabbed the vibrator that I'd enjoyed up my ass a couple of days earlier. As I watched, she turned it on and alternated between running it over her clit and thrusting it in and out of her pussy. As much as the show was for me, I knew she'd enjoy it too and it wasn't long before she'd cum twice more. When she noticed that I was fully hard, she set the vibrator aside, gently pushed me onto my back and then straddled me so she could lower herself onto my hardness. She rode me like that for a while, with loud moans each time she came. Eventually, she rolled to her back, pulling me with her. With me on top, I was able to raise her legs slightly and get much deeper, harder thrusts. Having already cum earlier, I knew I'd be good for a while so we had sex like that for almost an hour with me varying the speed, depth and force of my thrusts to bring her to as many orgasms as I could. Finally, Emma looked at me and said, "I know you're close, fill me up!"