Fun up North - Day 1

Where to start? Well, it was winter and like every winter I would head up North to go skiing. There were a few different families that we knew, we all had ski houses and we would all ski together. It worked out well for the parents because one family could handle watching the kids while the other adults could go out and party. All of us were very close and it was not uncommon to stay over at each other’s houses for a night or even more. It was on an occasion such as this where this story begins.

It was President’s Day, three families had all spent the weekend up on the mountain but some would have to go home due to school and work. There were only a lucky few of us who either didn’t have school or took the week off from work. The group was made up of one of my very good friends Eric (his parents and siblings had to head home,) my friend Joe’s mom, Denise, and me. Denise was a recent divorcee, her ex-husband had custody of the kids during this week, so she took the week off from work and was stuck with watching over me and Eric.

Now, as soon as Eric and I knew that we were free from family this week we knew we could get away with much more than usual. Eric was 18, same as myself, and a very fit young man. He had dark black hair, tight abs, solid arms and a nice set of skier’s legs. We had known one another our whole lives and shared many of the same interests.

Denise was a cool chick, she was in her mid-forties, her son Joe knew me and Eric well and as nice as he was, personally I was glad he was gone this week. I had always had something for his mom. She stood about 5’5” she had a little weight on her, but not what you would call fat, just curvy and with a huge set of tits and a lovely, round ass. She had long brown hair that was wavy and went to her mid-back. While growing up around her she is the only friend of my family’s that I found myself truly attracted to. She had a flirtatious way about her and a young spirit. Needless to say, Eric was also drawn to her. I know this because we had to split a room and more than once we would stay up late at night telling stories to each other, stories about girlfriends, first times and fantasies, many of which would include our friend Joe’s mom. It was during those late nights that Eric and I started getting so hot we went from talking about our fantasies to helping each other out with them. Nothing too far at first, just lending a hand to a friend in need, then lending a mouth and then maybe a more. We were just two young men, very horny and maybe a little curious.

Anyway, back to the story at hand. The day after everyone left it was just the three of us. Eric and I woke-up and Denise had already made breakfast for us. We chatted about what we would be doing that day, Eric and I were skiing and Denise was going to stay home to clean and exercise. She asked us to pick up groceries and some wine (we were just 18 but we had ID’s and guessed we’d be okay.) Eric and I set out and skied all day: it was cold and snowy but it seemed like we were the only ones on the mountain. While on the lifts we talked about Denise, I was the first to joke that maybe we could get her in a threesome, Eric laughed at the idea but I knew he was secretly thinking the same thing. I quickly changed the subject to the fact that we hadn’t gone sledding in years and that it might be fun to do some time that week.

Around 3:00pm or so we decided we had skied enough and that we should pick up some groceries and head home. While at the store Eric picked up the items on the list while I went a la carte. I picked up multiple bottles of wine, some beer, vodka, and just for fun some condoms and some KY jelly. I didn’t think we had any use for them but I thought it would be quite a sight when Denise would pull them out of the bag…and it was.

When we got back home Denise was in her workout clothes, a jumpsuit with maybe a sports bra underneath. She laughed at all of the booze we had bought and Eric made a slight comment that the more she drinks the better we look. Denise fired back that it was more like, the more she drinks the better our odds will be. Eric and I just looked at each other surprised and I could feel my cock shift in my pants. The tension then rose even more because directly after making that comment, Denise pulled the condoms and the lube out of the bag. Her face turned bright red, Eric and I had no other reaction than to laugh. I told her I put them in there as a gag and I apologized. Trying to save face Denise quipped that Eric and I should enjoy using these on each other, a comment that just made us both smile. To change the subject I said, “Let’s go sledding!” Denise felt that she was too old and told us to go ahead without her; we insisted that she must come even if its just one ride. She said she would think about it and might meet us down at the hill.

Eric and I grabbed two sleds and headed to our local hill. The hill was in a meadow not far from the house, it was quiet and secluded and very private. Eric and I cracked a few beers and threw ourselves down the mountain a couple of times; then, out of the blue, Denise decided to show. We cheered her appearance and told her she had made the right decision. She had a beer with us and we talked about how great skiing was that day and then she asked a very direct question, “Do you boys have girlfriends up here?” She knew that we had plenty of girls back home but still asked about up in the mountains. This question, whether innocent or not, seemed to change the mood of the day, if not the week.

We mentioned that there really wasn’t that much talent in the local pool. She said she was sorry to hear that and then joked we both must both be so horny. I said that we were, it was so difficult being young and in our sexual peak and with no one to help us. Eric followed immediately with the question, “When are women in their sexual peak?” Denise said ‘somewhere around thirty’ so I responded “Wait, aren’t you somewhere around thirty?” She blushed, looked up at us with a smile and said that she was too old for us, but “that she could teach us a thing or two.” Eric, always the jokester, said that he could teach her a thing or two about sledding and she said she doubted it.

We only had two sleds and we chastised Denise for not bringing one of her own. We realized that this might not be that bad and that one of us would have to share with Denise each time we went down the hill. First was Eric, he sat on the back of his sled and told Denise to sit in front of him and to hold on tight. She did as told; she sat right down, pushed her ass right up against Eric’s package and grabbed onto both his upper thighs. She leaned over her shoulder and said, “Like this?” Eric’s voice cracked when he answered that she was just fine and they shoved off. I followed right behind, we picked up some great speed and towards the bottom lost control and all had to bail. We rolled in the snow, laughing and truly enjoying ourselves. After regaining our sleds and getting back to the top of the hill Denise said that this time she wanted to go head first, she grabbed my sled and I said I would wait. She lay on her belly and turned and asked me why. I said that only one person can go at a time like that. Her response was, “I have had worse rides, jump on.” I said, “Okay” and I got right on top of her, the sled was long enough but I made a point to grind my crotch right against her ass. With my feet on the ground I rocked us back and forth; I knew everything I was doing with my friend’s mom was completely wrong at this point. Grinding against her I said, “1,2,3…” and before I could said ‘go’ she said, “lets just go on ten.” I wasn’t about to miss this opportunity so I kept grinding against her, my cock grew completely hard and Eric just stood there smiling. Eventually, I pushed off and we made it down the hill. On the way back I up I used the sled to cover my massive hard on.

When we returned to the top of the hill, Eric was there and he looked at Denise and said “that looked like fun.” Denise said that there were more ways than that to sled down the hill and commanded Eric to lay with his back on his sled and his feet pointing down the mountain. Denise then continued to sit right on top of Eric. Her tight snow pants looked great as she slowly grinded her crotch against what must have been Eric’s rock hard cock. The two stayed like that for a few seconds until she pushed off and they went down the hill. On their return I could see Eric was still rather excited. We opened another round of beers and I remarked that it seems Denise really could teach us a thing or two about sledding. Eric then said, “Have you ever gone sledding with two guys at the same time?” Her eyes lit up and she said she hadn’t, but that it sounds like so much fun. She once again commanded Eric to lie on his back; she mounted him and then asked if I would “get on from behind.” My cock shot to attention, making a noticeable tent in my pants. I got right behind her, grinding my cock and against her ass, her ass grinding against Eric and then, we were off. We didn’t make it more then a few feet before we all toppled over and rolled a few feet down the hill. I awkwardly laughed and realized how thick the sexual tension was. Denise popped right up and said, “That was fun, I’m going to go get dinner started.” And just like that she headed home like nothing happened.

Eric and I had one more beer and discussed what just happened. We walked back to the house and both confessed how worked up we both were.

Upon returning to the house we found that one of our two bathrooms was filled by Denise taking a shower. I knocked on the door and she said she would start dinner soon but she really needed a long shower after all that sledding. Eric and I knew what she was doing in there and we just smiled and said we would go downstairs and get cleaned up. Eric stripped down in front of me getting ready for a shower, his cock was semi-hard. It was a fabulous piece, it wasn’t terribly long but it was massively thick. I started to strip down and then asked, “what do you think is going on upstairs in that shower?” Our minds raced as I watched Eric’s cock come to full attention. I grabbed his towel and threw it on his rod, it hung there and he just laughed and walked into the bathroom as a human towel rack.

Now as the only one not in a shower I crept upstairs and tried to listen into Denise’s shower. I could make out the sounds of definite movement; it alternated between a slight slap and a good hard rub. My mind went wild thinking about my friend’s mom, violently rubbing her clit thinking about me. Maybe she was caressing he huge tits, squeezing her nipples working herself to orgasm thinking about me laying on top of her. Maybe she was fingering her tight ass, with the idea that she could be filled with two young men. Maybe.

I got myself too worked up, I was about to explode and I needed to. I went back down stairs and walked into the bathroom. Eric was still in the shower, I stripped down to nothing but an erection and I walked towards the shower. “I’m so fucking horny. I can’t stop thinking about Joe’s mom. I think I’m going to explode.” I said. Eric stuck his head out of the shower, looked me up and down, moved the shower curtain to show me how rock hard he was too. He told me he could not stop thinking about her as well; how much he wanted her mouth around his cock, how badly he wanted to hold her down and fuck her. I couldn’t take it, I said, “I’m coming in.” I turned off almost all of the lights in the bathroom and I slipped into the shower. It was very dark, I could barely see Eric. I said, tell me what you want to do with Denise. Eric went into detail about his fantasy of taking her upstairs in his parents bedroom. I reached down and grabbed his thick cock. I began stroking it nice and slow for him. He responded by thrusting his hips at me, I could tell he liked it. He continued on his story on how he wanted to pound our friend’s mom in every position available and while he was talking I continued to stroke him. I tried to be coy and while stroking I dropped to my knees; with one continuous motion I now had his cock in my mouth. It was so large it was difficult to fit all the way in; I tried to fit as much as I could while still using my hands. At this point he stopped talking and just focused on getting off. I worked his cock, back and forth, in and out; he used my mouth, thrusting his hips in tempo. After about a minute I could tell he was going to blow, I pulled his cock out of my mouth and continued to jerk him off under the flow of the shower. Since it was dark I couldn’t see where his cum was shooting but I knew that the shower would clean it up; his cock jerked back and forth in my hand, he started to grunt and then as quickly as it began, it was over. He pulled his cock back, I stood up and he said, “Thanks, I needed that.”

I was still there, still hard as can be. Eric said, do you want me to help you with that? I whispered “what do you think?” He leaned over and said I know what you want, you want to fuck Joe’s mom up the ass, don’t you? He knew that while I had had many girls our age, none of them let me in the backdoor. Eric had dated a few sluts that let him do it and I always loved hearing his stories about how tight their little asses were. Eric continued, “If we get to fuck her tonight the ass is all yours. But you have to be ready, I don’t want you to cum too soon.” With that he reached down and grabbed my dick. He started to jerk me off, it felt so good to have contact there. He gripped me hard and stroked me slow, he told me to picture Denise on all fours, her massive tits hanging there and her tight little asshole just waiting for me. Waiting for me to stick my hard cock deep inside, to slip into its new tightness, to feel Eric’s cock in her vigina at the same time. With that I lost it. I shot a massive load, it covered Eric’s hand and probably his belly. We both cleaned off, I turned the lights back on and we toweled off, feeling slightly less horny. But I couldn’t get what he had said out of my mind, the idea of feeling his cock fucking Denise’s pussy while I was fucking her ass almost made my dick spring right back up.

As we walked back upstairs Denise was just preparing dinner. She was wearing a nice pair of sweat pants that perfectly accentuated her curvy ass and a zip up matching top which revealed some lovely cleavage. As she was working in the kitchen I started to make some drinks for everyone, you could tell that all of us were much more relaxed after our showers and I thought some stiff drinks could help even more. I think we each had a few cocktails before dinner was ready. At dinner we opened some wine, talked about how great it was to be away from home for awhile and just everyday conversation, until Eric brought up Denise’s recent divorce. She didn’t really mind, she told us she was glad to be single but the worst part was being back on the dating scene and how long she had now gone without sex. I chimed in and said it had been awhile for me and Eric too (which wasn’t really true) and she countered that at least she has a few “vibrating friends” back home that would always help her in a bind. Eric said that’s too bad that they are back home and mentioned it must be frustrating this week. I think at this point she realized how far into her personal life we had gotten and she quickly changed the subject and asked to watch a movie.

Eric and I cleaned up after dinner while Denise picked out a film, it was some old movie that Eric and I hadn’t seen but we were more than willing. She started the film and sat in the love seat, Eric walked over and took the lounge chair and I opened another bottle of wine and walked over to them. When handing the glass of wine to Denise I asked if the seat next to her was taken she said she would be delighted to have me sit next to her but asked that I turn down all the lights so we could truly enjoy the movie. I did as told and sat as close as possible next to her on the love seat. The film was unmemorable and rather basic, but about half way through there was a nice sex scene between two of the characters, at this time Denise moved a hand onto my leg and moved it up onto my inner thigh. She continued to move it closer and closer to my now rapidly growing package, she moved it up until she was right at my balls, she cupped them and gave a nice squeeze, and she then slipped her hand to my obvious hard-on and gripped it tightly. She moved in at this point and leaned over to my ear and said, “Oh, excuse me, I think I need more wine, can you go get some now?” Oh, my lord is this woman a tease! I got up, adjusted myself and went to pour her more wine, on my return I came up behind her, leaned over her shoulder and said, “I got you your wine, is there anything else you desire?” At that point, I handed her the wine over her shoulder, letting my hand and arm firmly rub against her colossal chest. She looked up at me and just smiled and said, “Thank you, come sit down, the film is almost over.” We both sat there without touching each other for the next 20 minutes or so; again, the sexual tension just continued to grow, I could think of nothing more than tearing off her top and sucking on her beautiful tits.

As soon as the film was done Denise excused herself to the bathroom, during that time Eric came over and asked how the handjob was, I told him she is a major tease and our work was cut out for us. Eric smiled, opened another bottle of wine and said he thinks he has a good idea. When Denise walked back into the room Eric handed Denise another glass of wine, we all sat on different couches and started talking and drinking, the conversation was at times sexual, but mostly it was just talking about mutual acquaintances that we had, things we liked, etc. The wine continued to flow and I think this was Eric’s plan, one bottle, then another and another. Eventually we were all tipsy and horny and that’s when Eric asked, “Who wants to play a game?” Denise and I said yes almost in unison. Eric said, “Anyone like Truth or Dare?”

We all sat on the floor, lights very dimmed by Eric (great thought,) the fire going and just the hint of light falling snow outside the window. The cycle for asking questions and issuing dares went from me to Denise and from her to Eric and Eric back to me. I went first and asked Denise, “Truth or dare?” She picked dare. I mentioned that with the fire going and the heat turned up that she looked pretty hot and she should probably take her zip-up top off. She agreed that she was hot and she got up on her knees and slowly unzipped her top, underneath she was wearing only a tank top with no bra. Her amazing tits seemed to just get bigger, they didn’t sag or anything, they just sat there, perfectly. Her nipples grew hard, you could see them right through her top, she reached up and squeezed one lightly while looking right at me. She said, “for how hot it is here, it looks like my girls are cold.” She then sat right back down, and asked Eric, “Truth or dare” He picked dare. She said he looked hot and that he should take his shirt off too. He did so without delay. His chest and arms looked great, Denise just sat there staring and smiling as if she was so happy with what she had in front of her. Next was my turn and of course I chose dare, Eric continued the challenge that I should remove my shirt, which I did in no time at all. Now, it was back to Denise. I posed the question and again she picked a dare, I mentioned that we all looked so comfortable but it was still pretty hot, so I dared her to take off her pants. She gave me a sly stare and a slight smile and said, “Well if that is my dare.” With that she jumped up and turned her back to Eric and I, who at that moment looked at each other like it was Christmas morning and we were about to open our first gift. Denise put her thumbs in her waistband and slowly started to shimmy out of her sweatpants, little by little we she started to reveal a nice red lace thong covering her beautifully round ass. The lower she got with her pants the more she bent sticking her ass out towards us, it was just beautiful. She stopped, and turned and kicked her pants right at my head and then sat down and asked Eric, truth or dare? He picked dare. She told him to remove the shorts he had on, he grinned and said that wouldn’t be a problem, but he let us both know he wasn’t wearing any underwear. At that mention Denise said, “Fine, then I change the dare. I dare you to show the two of us what you have under there, and we want to see you at full attention!” Eric popped to his feet and slowly pulled his shorts down to reveal a thick but not hard cock. I was amazed because I felt like I had been hard all night, I couldn’t believe he wasn’t busting through his pants. Denise looked at it in awe, she licked her lips, blinked a few times and then mentioned that he hadn’t fulfilled the dare, she said he had to be all the way hard. He grabbed his thickness and grinned and said, “You are right.” and then he asked me, “truth or dare.” I chose dare. Eric then dared me to go over to Denise, take off her top and to suck on her fabulous breasts. He said that would probably do the job. I looked over at Denise, she looked right into my eyes and said, “Well, it is a dare.” I moved over to her and started kissing her neck; she immediately threw her head back and started to sigh. While continuing to kiss and suck he neck I slipped one strap of her tank top off her shoulder and then another. Moving my hands down I softly caressed her massively large globes and then with one quick motion, I pulled the tank top down exposing the largest, most immaculate set of tits I had ever seen. I moved my mouth slowly between both nipples, licking around her areolas, sucking on her nipples and then removing my mouth to blow gently against them, causing immediate hardening. Speaking of hardening, I looked over at Eric who was now stroking his wide, rigid cock. He gave me a head nod, at that I pulled away, I looked at Denise and I said, “Truth or dare?” She looked at the two of us, and quietly answered, dare. I leaned into her and said, “I dare you to let us both cum inside you at the same time.”

We moved Denise off the floor and onto the lounge, she sat there and looked at my shorts, I pulled them off exposing my fully erect penis. She motioned me towards the lounge and I sat at her feet, she asked for help getting her panties off. I moved slowly slipping them off, Eric stood at the side of the lounge, both of us staring in excitement waiting to see our friend’s mom’s pussy for the first time. She had a little tuft of hair above her clit and that was about it, the lips were wide open and glistening with her excitement. I spread her legs and moved my head into her enveloping aroma. Looking up all I could see was her lovely breasts and then Eric moving his cock towards her head. She reached up to grab him, she stroked him and few times and commented about how wide Eric was, and then she moved forward and took his manhood into her mouth. I started slowly; I barely touched her clit with my tongue, just letting the least bit of contact tease her. I then moved my tongue slowly down both of her lips and then back to her clit, after hearing her audible pleasure I moved lower, sticking my tongue into her pussy, moving it up and down inside of her, she moaned even louder this time, but it was muffled by the fact that she had my friend implanted in her mouth. I replaced my tongue with a finger, slowly and deliberately fingering her g-spot. At this point to say she was wet would be an understatement, she was soaked, her vagina was begging for more and more. I gave her another finger and then started to suck directly on her clit, I slowly built up speed with my fingers and pressure with my mouth, she moaned and moaned and started to writhe back and forth, back and forth until I felt her spasm around my fingers. At that point I sat up and looked at her slowly sucking my friend. She pulled him out of her mouth, looked an me and said, “thank you.”

Eric and I now stood at full attention next to our friend’s mom, she had just finished a massive orgasm and now needed more. She looked at us and said, “I need someone to fuck me right now.” Eric moved rapidly between her legs and I moved to the top of the lounge. She strained her neck to turn and try and see me and told me she couldn’t reach me, I told her there was a simple solution, “flip over and suck my dick while Eric fucks you from behind.” She gave us a big smile and assumed the position. She moved her head towards my cock while Eric saddled up behind her. She grabbed my dick, and stuffed it in her mouth; it was so wet and so inviting, within a few head bobs she had swallowed my entire dick. Eric could see how much I was enjoying it and said, “She’s one great cocksucker isn’t she?” I could do nothing more than moan as an answer. Eric grabbed his prick and rubbed it up and down Denise’s now sopping vagina and with one fell swoop he jammed his broadness deep inside of our friend’s mother. She let out a moan that was a perfect mixture of ecstasy and ache, her eyes closed tightly shut while my friend continued to put his full pressure into her cunt. She pulled my cock out of her mouth, took a deep breath and looked up at me and said, “That is some cock.” I just stood there, smiled at her and pushed the back of her head towards my dick. I looked at Eric and said, “I think she likes it.” And with that he started to move in an out of her. He was slow and deliberate at first but slowly started to build up steam until he was pistoning himself in and out of her with reckless abandon. After about one minute of watching this I was so close to cumming I had to pull myself out of her mouth. With nothing muffling her screams she let it all out, she was moaning like she hadn’t had a good fuck in months, if not years (which could have been the case.) I slowly walked away, not that either of them noticed and slipped downstairs to grab the lube we purchased earlier that day.

When arriving back upstairs I could see and hear that Denise was having another orgasm, her knuckles were white while she grabbed the couch and held on while truly enjoying a massive orgasm. Eric, sensing she just came, slowed and then withdrew himself from her; he was still as stiff as before and I was amazed he didn’t cum. Denise flipped onto her side and tried to catch her breath, Eric stood up next to me while I hid the lube behind my back. Denise said that she hadn’t cum like that in years and said thank you to us both, I told her don’t worry about it but she still had to complete her dare and I presented the bottle of lube from behind my back. She flashed us a devilish grin and said it seems like we almost planned this out. Eric took the initiative and laid on his back on the ground, Denise got up and moved, standing over him. She looked at Eric then looked at me and said, “This will be my first time with two men in me at once, please be gentle.” And with that she lowered herself onto Eric, he slipped right back in and she let out a little moan. I got down on my knees with Eric’s legs between mine and I moved my head over to her ass, my hands massaged her cheeks, slowly moving them apart exposing a striking little asshole just waiting for me. I couldn’t help myself, I moved in immediately and started licking her tiny hole, I moved my tongue in little circles, and I lightly probed her sphincter and then started licking up and down. Every time I went from down to up I would let my tongue hit Eric’s shaft and continue all the way up. Denise was going wild and Eric didn’t seem to mind himself. The two started to pick up the pace of their rhythmic rocking. I positioned myself back up on my knees, I grabbed the lube and greased up my eager poll. I told Eric to slow up for one second; I put my left hand on Denise’s hip and put my right hand on my shaft. I moved the head up and down until it was directly in line with her taut asshole. This was it, I was about to fulfill numerous fantasies at the same time, I was about to fuck my friend’s mom in the ass while my other friend is pounding her pussy and we both will fill her with our cum. I couldn’t wait.

I pushed the head of my cock slowly against her ass, Denise responded by pushing back towards me. My cock head started to disappear, her ass slowly started to engulf my manhood. It was so tight; it was a slow go at first. I moved inch by inch until, pop, I slipped all the way in with one motion. Denise let out a whimper and then a deep breath and then Eric started to move. It was amazing, with both of us buried in Denise’s holes I could feel his bulbous, throbbing cock rubbing against mine. I started to move slowly, pulling out my length, almost the whole thing and then slipping it back inside her now inviting cavity. Eric and I continued to move back and forth, in and out, until we came to a perfect rhythm where Denise always had one of us deep inside her and the other would be pulled most of the way out. We moved like this, all three of us writhing with passion, Denise was moaning, Eric was grunting and I was enjoying the sexual choir we had now created. After about two minutes or so, I couldn’t take it. I cried out that I was going to blow; Denise threw her head back and said, “I want you to cum in my ass. Fill up my little hole.” At that Eric grunted and said he was going to cum. Denise screeched with pleasure, knowing she was about to receive multiple cumshots into her pussy and ass. Eric grunted his teeth and closed his eyes and thrusted as hard as he could into her. I was deeply buried in her ass and I felt him start to cum, that pushed me over the edge, I couldn’t take it, I pulled out one more time and cried out a guttural moan and then shoved my cock as far into Denise as possible. I felt myself explode, spasm after spasm of pleasure was only compounded but the feeling of Eric’s cock doing the same. Denise cried out that she too was now cumming and I watched her knuckles get white as she dug her nails in Eric’s shoulders. After about a minute we were all just there, connected and breathing heavy. I leaned back and slowly pulled myself out of Denise; Eric followed and I could see the cum starting to drip out of her. We rolled over and lay on the floor, no one said a word, after a few minutes, Denise got up, put on her pants, grabbed her top and said, “Thank you both very much, I’m going to go to bed but this should be a fun few days.” And with that she walked into her bedroom and closed the door.