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Jeff and Lisa Miss Ski School

Category: Mature
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My name is Lisa; I will be 19 years old at the end of the year and I can boast a 36-24-35 body, if I was into boasting. I am often mistaken for being at least three or four years older than I am; if I was taller it would probably be more. I suppose that when I get older the age factor might be classified as a problem, but for the moment it doesn’t bother me in the slightest. I like being young and I like being mistaken as older.

I thought that I wanted to be a blonde when I was younger, but I’m now more than satisfied with my long brown hair. It looks like something from a hair shampoo ad’ when I wash it, so I’m proud of calling this my ‘best feature’. All my friends have mentioned just how much they envy me and my looks, but I have never been a poser or a big-head so I just thank them for their comments and leave it at that.

Although I wouldn’t say I have a lot of experience when it comes to sex I have had enough boyfriends to know what I would consider as good and not good. Most of it has been the not good variety. I must admit to myself that I do like older men. I fantasize about them a lot of the time. I get a bit fed-up with the antics of the young guys in college, they all seem to fit into the same mold and I don’t seem to enjoy that category.

Most of the younger guys seem to have the attitude that they are the best thing since sliced bread; but with many of them they are simply hopeless when it comes to treating a girl properly. I’m not talking about opening the car door for me or buying dinner and stuff like that; I’m referring to sex, making love, call it what you will. In the times that I have been with boys of my own age I think I have had one orgasm; this event happened with me doing most of the work on my clit while this boy, Gilbert, pushed his rather small cock in and out of my pussy until he was grunting and groaning like he had it trapped in a door. Not the best of memories.

I have this fantasy that when I lose my virginity proper, in other words when the man includes me in the love-making, it will be a really distinguished older man who knows just how to push all the right buttons.


I went on a skiing holiday recently, my first holiday without mom and dad. This holiday was my first real experience as an ‘adult’, it felt like I had been let out of jail. This doesn’t mean that I had a bad time at home, or anywhere else for that matter, I just believed that I was missing out on something… although I had no firm idea what. As we boarded the bus to the ski resort I couldn’t help but think about my fantasy of an older man.

The two girls that went with me on holiday had been friends since we were ten years old. I was the most recent arrival into the neighborhood and we all seemed to hit it off straight away. We had since been in the same classes at school, we were all currently dabbling at cheerleading and we didn’t have too many secrets from one another. All in all we got along great. With their make up on my friends also looked at least two to three years older than their present 17 years.

We planned to be at the ski resort for five days, arriving Sunday evening and leaving Friday lunchtime. Stupid timing, but it made it less expensive for us. We had been saving hard all year for this holiday, so we were going to make the best of it while we were there. People who came into the hotel at the weekend paid almost the same amount for the Friday and Saturday evening as we were paying for five nights, this didn’t make sense to us; we wanted to use our spare cash for partying and skiing.

We went down to dinner immediately after unpacking and the hotel dining room was half full already; the people already there looked as though they had been out on the slopes all day. Many of them would not be too long out of bed from the look of them, most of them looked exhausted.

Surveying the room I couldn’t help looking hard at all the men to see if there were any that fitted into the category that rang my bell… the distinguished, single, older man; the one that might be able to show me just whatever it was that I had been missing while I had been messing around with the young college students.

A quick hard scan of the room showed that I wasn’t in luck this time.

The hotel had an a la carte menu, if this was what the guests wanted, but they also had a smorgasbord meal where people simply got in line and chose whatever they wanted from a fantastic array of food, just like at college – but ten times better. The smorgasbord came at a price that was usually far less than the a la carte meal. There were quite a few people in the line.

All three of us joined in the line, me at the rear. I then caught a glimpse of what I’d been fantasizing about as I was idly looking around at the food displayed in front of me. He came into the dining room and took a place in line right behind me. He looked to be in his late forties or early fifties, with graying hair at the temples and a tan that had taken a lot of sun time to achieve. He was well over six feet tall and was obviously very fit.
His wide shoulders and narrow waist did not go unnoticed. His clothes were in shades of grey and black, except for the white lettering around the neck of his turtle-neck sweater; it was a logo of some sort, probably a ski maker. There was no doubt in my mind that everything he was dressed in was expensive, and he’d spent some time choosing them. This was like an identi-kit picture from my fantasy, come to life. He looked good enough to eat; literally.

I quickly looked toward the front of the line, a little embarrassed; I had been staring at this man like I was a bitch in heat. I wondered what he thought of the way I had looked at him. He said, “Hi” as I couldn’t help turning my head again to get another eye-full.
“Hello.” I said in return, feeling like an idiot as I spoke.

I collected my food and rushed to the table where my two friends were. I almost fell as I sat down with a thump. They could see that I was flustered and wondered what had caused the color in my cheeks to change to a couple of shades less than bright pink. They looked around but didn’t notice anything that might bring upon my sudden state of embarrassment. They were interested to know why I had rushed back from the counter but not that interested to continue with questions, we left it at that and no more was said.

When I got back to my room I undressed, jumped into bed and before going to sleep I fantasized about my older man. As I closed my eyes I dreamed of a very fat cock forcing its way inside me. I finished up having a wonderful, no frills, orgasm while playing with myself.

All three of us had enjoyed a good night’s sleep and we got an early start to the slopes. We wanted to get in a full days skiing, so we were on the road at 7.30. The weather looked like something from a picture-postcard; a great start to the holiday. Something I didn’t know was that my first day skiing would come to a halt just over three hours.

With not training specifically for skiing before I left for the holiday, it didn’t take too long for my thighs to begin to ache. They then began shaking from the unusual stress of skiing down the slope for the third time; then a few moguls later I was on my back with my ski’s facing up the hill and my head facing the opposite way. Snow began making its way down my pants to the crack in my ass. My ankle had taken a bad turn and my back felt as though I had strained a few of the muscles alongside my spine. All-in-all I didn’t feel on top of the world. I crawled around to a position where I could get back on my feet and with a struggle I stood up.

As my friends arrived I thanked my lucky stars that it wasn’t worse, and said the same thing aloud to them as I told them what had happened. I said that I would have to call it a day, go back to the hotel – have a hot bath or a spa, and rest up for what was left of our first day. I said I’d catch up with them at about 6.00pm when they returned from the slopes.


I arrived back at the hotel just before lunchtime. I put away my skiing gear then went down to the hotel bar for a coffee. As I went into the bar my fantasy-man from the evening before was there enjoying a cappuccino. He smiled, looked at my slight limp as I walked in and said, “Trouble on the slopes?”

“You could say that.”

“What happened?”

I explained about the lack of ski fitness and the fact that I stumbled through a couple of moguls and I was feeling slightly silly, as well as sore. I told him that I’d decided to call it a day rather than chance hurting myself further.

It turned out that my fantasy man was called Jeff and the reason he was in the bar, not out on the slopes, was because he had been at the hotel a week already and he wanted to have a day without snow and too many people around him. I thought, “Well that’s OK with me!”

Jeff asked my name and I said, “It’s Lisa.”

“You know Lisa, the thing you should be doing now is having a nice hot bath, then a warm oil massage. You will feel a hundred percent better when that’s finished.”

I didn’t say anything about his comment, and then asked the barman for a coffee. I have to admit, the recommended massage treatment sounded fantastic. I was sure that he would raise the subject again if he was really interested.

For the next half hour we talked as though we had been friends for a long time; absolutely nothing like the conversations I’d had with my male friends at college. I knew that there was every chance that my fantasy might come true if he was as good at everything else as he was at holding a conversation.

I found out that Jeff’s wife had died the previous year; they didn’t have kids, so when she was gone he was left on his own. He was fit, successful and lived in a really great part of the same city that I was born in and now lived in. His fitness came from visits to the gym every night of the week, and running and cycling at the weekends. This was the first time he had stopped work for long enough to take a holiday since his wife died. He felt that working was one way of getting over his wife’s death.

It had taken him almost a full year to come to terms with the fact that he must get on with his own life. He didn’t make a drama of the situation when he told me, he just explained it the way it was. He had not been with another woman in the time since his wife died and his business had kept him so busy that he rarely thought about sex. “Maybe only once or twice a day,” Jeff said with a cheeky smile on his face. I didn’t feel in the slightest bit pressured from our conversation, in fact it made me feel more assured that he really was my fantasy come true.

I decided that I had better have the hot bath that had been recommended, and I had promised myself, or the aches and pains would still be there tomorrow and cut a large hole in the available holiday time.

Having finished my coffee, I looked at Jeff and said, “Well, I’m going to take your advice and go for that hot bath. It’s a pity that the hotel doesn’t have a masseur and I could afford to use him.”

“Just give me a call when you’ve finished your bath and I’ll bring the oil. I’m in room 571 when you’re ready. I’m a pretty good masseur when I put my mind to it.”

I smiled, said that I might take him up on his offer and walked away as calmly as I could. My insides were doing somersaults and back-flips. I wondered if I would call room 571 when I’d finished having a bath or not.


When I got back to my room, I felt a bit of a chill; probably from seeing the snow outside the window. I turned the thermostat up by 10 degrees and then began running the bath. A ‘bath-bomb’ that I’d brought from home had the foam a good foot above the bath before I knew what was happening. I couldn’t help but think about Jeff’s offer as I stripped off my clothes.

Standing in the bathroom for a little while before jumping in the bath, with clouds of steam making the place warm, helped me to make up my mind. I stepped out of the bathroom, picked up the phone and called 571.

“Hello Jeff, it’s Lisa. I’ve decided that I’d like to take you up on your offer of the massage. My body is aching a bit and I think it would do me good to try to loosen up. I’m in room 633; come up in half an hour, I’m just about to jump in the bath. I’ll leave the door off the catch so you can come in when you arrive.”

“OK, see you in half an hour.”

My heart was beginning to thud at a rate that felt like I’d been exercising hard, I could feel it loud in my ears. I went back into the bathroom, stepped into the hot water and slowly sat back. I lowered myself down into the water, with the foam in line with my eyes. I cleared a patch with my arm and lay back to enjoy the soak.

Not more than fifteen minutes later I heard the door of the hotel room open, and then close again. “It’s me Lisa – Jeff.” I heard. “I know it’s not been a half hour but I knew that you’d be in the bath anyway, so I thought I might as well come on up. I hope that’s OK?”

“Yes that’s fine, I’m going to soak for a while longer, so help yourself to a drink from the mini-bar if you want one?”

“No thanks; I thought you may want to relax a bit, so I brought over a bottle of bubbly as well as the oil. You’re welcome to a glass while you’re in the bath if you’d like one?”

My heart was now going like a trip-hammer and my imagination must have been running away with me because my pussy was beginning to feel warm and wet… on the inside as well as the outside.

“That would be great Jeff; there are glasses in the cupboard above the mini-bar.”

A few minutes later the door to the bathroom opened and Jeff stepped inside with a glass of champagne in both hands. He laughed as he saw the height of the foam rising from the bath water. “My God, what are you doing in here? It’s like a frozen relief of Niagara Falls!”

I couldn’t help laughing with him; the foam must have looked even higher from where he was than from my position. As I reached up to take the glass I grabbed the side of the bath and then slipped. I went down into the water a lot quicker than I did when I was getting up; water cascaded over the side of the bath. I couldn’t help but grab for anything that would stop me from either dropping the glass or going under the water totally. My left hand continued to hold the glass, my right hand grabbed for the side of the bath – flattening the foam level with the water as I did so. I came up like a cork as my right hand gained purchase and I was sitting upright in the bath, having regained my balance. Of course the last thing I was thinking about was the fact that Jeff was getting a good view of me from the waist up.

“Well, what do you do for an encore Lisa?”

I looked at him, looked at myself, and began laughing again. “I don’t normally do this for visitors to my bathroom. In fact you’re the first and only one.”

“I’m glad about that. Here, let me help you.”

Jeff took the glass from my hand and placed it on the window sill with his own glass. Then, taking my left hand, he helped me to stand, making sure that I wasn’t going to slip over again. There was foam all over me, Jeff turned around, grabbed a large towel, handed it to me and went back into the main room, picking up the glasses of champagne as he left. He put them down on the coffee table and came back to grab a second towel from the rack.

I wrapped myself in the towel he’d handed me, then went out to join him. He had already placed the towel he had across the bed, close to the end opposite the head-board. He then returned to the bathroom and set the hot water running over the bottle he’d placed in the sink to heat up the oil. A few minutes later he said, “OK Lisa, loosen your towel at the front and lie down on the towel on the bed and relax while you’re still warm. How are the aches and pains?”

“They feel fine at the moment, but I must admit I am looking forward to my massage.”

As I began loosening the towel around me, I noticed the bulge in the right hand side of Jeff’s slacks. It looked so big that I thought for sure that he must be joking and that perhaps he’d placed something in there to make it look that much bigger. I don’t have any idea why I hadn’t looked or noticed this area before; perhaps because he was a fantasy and I didn’t ‘need’ to look because I ‘knew’ it would be exactly as I fantasized.

As I lay down on the bed I tilted my head to the side and looked again, this time I could actually see the outline of his cock. It obviously wasn’t hard, it was pointing in a curve toward his knee. I physically took a quiet gulp and began to wonder what was going to happen with my fantasy – before, after or during my massage?

When I got comfortable Jeff took a hold of the towel that had been wrapped around me, folded it in half and placed it across me, from my waist to my thigh. He went to the bathroom, got the warm oil and came back to the bed. I really was still achy from the mishap on the slopes so I relaxed my body, even if I was having a hard time relaxing my brain.

“Are you warm enough?” Jeff said.

“Yes, I’m fine.”

He then sat on the bed next to me and began to work the oil into my shoulders and arms. I didn’t know how to judge my first feelings as Jeff’s hands began the massage; I just knew that it felt good. He had been working for about ten minutes and was struggling to reach over to my right arm and shoulder. He asked if I would object to him getting a bit more comfortable; I heard myself say, “No problem, do whatever you need to.” I looked around and saw Jeff take off his slacks and button down shirt.

He wore a white T-shirt and a pair of black silk boxers. Looking at his body made me close my eyes and take notice of the strong signals coming from my pussy. Jeff was now able to get down to massaging in a way that was better for him and certainly more exciting for me. The first thing he did was to come around to the end of the bed where my head lay and, then – gently grabbing my arms, he pulled me further onto the bed.

As he did this I noticed that the curve in his previously flaccid cock had straightened out and was now taking the shape of a very large salami inside the black silk. I wasn’t sure but I could have sworn that I saw the tip of it poking out from the leg of his boxers. If this was the case, I thought, he has got one enormous cock.

Jeff went back around to the other end of the bed and without another word he straddled my legs and began working on my back again with solid strokes. It felt wonderful. What Jeff was doing to me with his fingers was starting to get me wet, I couldn’t believe it, this guy was going to make me come and he’d only touched my back and shoulders so far. I was getting so hot I started to grind my pussy into the bed with slow gyrations.

Suddenly Jeff slid his hand from my back under the towel and began to lightly stroke my ass. I rose onto one elbow, looked around at him in surprise. He smiled at me and said, “Is everything OK?” I nodded and relaxed. He then poured some more oil from the bottle down into the crack leading from my ass to my pussy.

The bottle was quickly put away and he continued rubbing my ass with one hand while the fingers on the other hand began to rub the puckered area around my asshole and the sensitive bridge between my asshole and my pussy. I didn’t know whose voice I heard making moaning noises but it wasn’t Jeff and as there wasn’t anyone else in the room. It must have been me.

After sliding his fingers up and down the lips of my now very wet pussy he began to move away and down to my legs, eventually to my feet. He kept an even amount of oil on all parts of my body without once creating an uncomfortable feeling.

When he had finished the backs of my legs and my feet he asked if I would like to turn over. I didn’t say anything; I just turned over and lay exactly where I had been lying when I was on my front. The towel was again covering my lower half around my thighs and pussy and my top half was naked. I presumed that Jeff would immediately go for my breasts, but he didn’t. He surprised me by beginning at my fingertips. He took each finger in turn and massaged every square inch of the finger, then each hand, each arm and each shoulder before he finally began to make small – then larger circles with his fingers on my breasts.

By this stage my pussy was so wet that I felt that my juices must be running down the inside of my leg. My nipples were a larger size than I had ever seen them, they must have been sticking out a half inch and they felt as hard as steel. The areola color was darker than the rest of the area and they were also swollen larger than I had ever seen before.

Once again Jeff’s hand slowly went under the towel and began to rub the oil into the top of my thighs, then my pussy, this time from the front side, not the back. As he did this my legs began to open a little wider of their own accord. First one, then two of his fingers slipped inside the lips of my pussy, then a third finger slipped in beside these and I was within a whisker of having my first full orgasm. I had felt slight tremors earlier during the massage, but now I felt a wonderful pressure begin to build.

The areas to each side of my neck began to tingle, my ears felt hot and the noises of slurping and suction coming from his fingers darting in and out of my pussy seemed far away. The heat around my jaw line quickly made its way to my nipples and rushed over my stomach. The orgasm was moments away and as his fingers turned over to allow his thumb to take pride of place tenderly rubbing my swollen clitoris, the three fingers continued their probing journey inside me. I knew that I was going to have a spectacular orgasm… even before he’d put his cock anywhere near me.

The orgasm burst over me like a dam being allowed to break free. I don’t know if I screamed or moaned, but I did hear someone that sounded like me as my nerve endings went ballistic. I don’t recall ever having feelings like this.

Moments after the last throws of my orgasm I felt Jeff’s legs move away from the position they’d been in, straddling my own legs. He continued gently rubbing the outside of my pussy lips as he stood up from the bed. He then lifted the T Shirt over his head and as I stared at his massive chest he began to take off his silk boxers. He smiled and asked if I liked my massage so far. I just said “Mmmmmm” and stared in disbelief.

The size of his cock was something that I will always find hard to describe. I’ve read magazines and seen porno on the internet where this guy has a cock this big and this one has one this round, but I have to admit that, unless they were taking their measurements from the asshole to the tip of the cock there is no way that some of these cocks were anywhere near the length they claimed to be. Some claimed to have 7, 8 or 9 inches, but there is no way that they are that big, who are they kidding?

This cock that Jeff had between his legs was like nothing I had ever seen or heard of before in my life. I put my hands out to touch it. I gently grabbed it at the base with one hand and even squeezing it I still couldn’t get my hand around it. In fact I was at least an inch to an inch and a half shy of my fingers meeting.

When I placed my other hand next to the first there was still room for at least another two hands the same size as mine before they would reach the end of his cock. This was a magnificent specimen of manhood. So far it hadn’t got completely hard, so there was still room for it to grow. Jeff put his hands to each side of my face, lifted my face upwards and kissed me. Our tongues met and danced with one another and I was feeling the stirrings of my next orgasm in the wings. We came apart for a moment and Jeff’s cock was only inches from my face.

I pulled his cock slowly toward my mouth and Jeff moved in with the pressure from my hands. Opening my mouth to the widest that it would go; I still had to force my lips over the knob, which then completely filled my mouth. As I started sucking, making more saliva, I slid my hands along the shaft; this started him moaning in ecstasy. His cock was now increasing in hardness and I was afraid it would become too big for my mouth. As my tongue got him wetter and he became slippery I started to squeeze more of him into my mouth, until finally I felt the tip touching the back of my throat. There was still a lot left outside, in fact a lot more than was already inside my mouth.

Jeff started to withdraw, but I tried to hold him in my mouth. I wanted to feel control over this huge cock. With a loud ‘plop’ he came out of my mouth, at last completely stiff. He removed the towel that was covering my pussy and thighs, and then pulled me toward the edge of the bed. Putting his hands underneath my knees he pushed my legs into the air toward my head and outwards. I felt the lips of my pussy fall apart and I was open to whatever Jeff had in mind.

A hot tongue then began to lick the whole length of my pussy lips and the feeling of my second full orgasm wasn’t far away, the tingling had begun again. As he enclosed my clitoris in his warm lips I began to shudder, my arms limply dropping by my side in surrender to this sensual onslaught.

While I was still away in orgasm-land Jeff pulled me even closer to the edge of the bed and leaned forward with his cock doing a self-seeking act on my very wet opening. I reached down and took hold of the beer bottle sized cock, guiding him into my pussy. As he pushed forward I felt my pussy lips being stretched further and further apart. What relief when they eventually closed around the knob!

Still holding onto him I was now writhing around in ecstasy, not comprehending how something this big could fit inside me. With small in-and-out movements he continued to force more into me until I thought that I would burst, then he settled into a slow rhythm of pulling most of his cock out, then pushing it all the way back in again. This was driving me absolutely wild. The fit was so tight that each time he withdrew I could now see my pussy clinging to his shaft. The sight was so arousing that I started coming again and bucked my hips against his thrusting. I reached the most incredible climax imaginable. I thought that what I had experienced in the first two orgasms was something else, but this made the others look like a brief practice session.

I didn’t think that I could take any more of this exquisite torture, but now I was so saturated that he began penetrating even deeper into my pink tunnel. I let out one low groan as I watched inch after inch disappear into me in one fluid motion. I didn’t think it would have been possible, but soon my pussy was wrapped around its entire length. Then Jeff stopped pushing and withdrawing and just let me feel the experience of being completely filled.

As Jeff let his cock slowly throb inside me my fourth climax began to build. I couldn’t help it; I started to thrash around beneath him. This had the desired effect as he began pounding into me again, his solid chest squashing into my breasts, the oil making wonderful obscene noises. Oh boy, I thought, I have never been fucked like this before… not even in my wildest dreams did I think this was possible.

Very soon we both cried out, “I’m coming!” at the same time. We ground into each other and I felt the pressure of his semen shoot up high inside me again and again. I watched Jeff’s face as his orgasm hit him and the look on his face was incredible. He looked as though he was having a battle between his crying and laughing emotions.
He slowly withdrew and another spasm wracked my body. He collapsed beside me, a look of sublime satisfaction on his face. I marveled at the size of his massive cock and moved down to lick all the combined juices off it, running my tongue the entire length of his meaty shaft. I wanted to finish by slipping his balls into my mouth, one at a time, but they were so big that I could only kiss and fondle them.

Jeff picked me up off the bed and kissed me so deeply that I felt that he could make my next orgasm happen just by doing this. My distinguished gentlemen had shown me exactly what I had been missing with the amateurish efforts of the college boys. I couldn’t wait for the next time.

I still had another four days of my holiday left and I felt sure that I would be able to convince my friends that my ankle and back were far worse than I thought from my incident on the slopes. I was going to need rest and recuperation while they were out skiing each day. “Of course I’ll be fine.” I assured them when they questioned me.
I might even have this problem when I get back home, after all that’s where Jeff lives to.

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