Lisa's Skiing Holiday

Lisa's Skiing Holiday

Hi, my name's Lisa. I'll be nineteen in November, but I could easily pass for someone in their mid-twenties. I suppose the age thing might bother me as I get older, but for now, it doesn't bother me in the slightest.

When friends have said they envy my looks, I've thanked them for their comments and left it at that. Since my early teens, I wished I was blonde, but now I'm happy with my shoulder-length dark brown hair. It looks like the adverts you see for shampoo, and it's nice to hear people say it is my best feature.

I haven't had a lot of experience when it comes to men. However, I have had enough boyfriends to know what I consider good and not good. Most have fallen into the 'not good' category due to inexperience. I often fantasise about older men because the young guys in college are so predictable. They have no idea how to treat a girl properly. I am not talking about them opening the car door for me or buying dinner; I'm referring to sex, making love, call it what you will.

I've had one solitary orgasm while with a boy my age. I furiously rubbed my clit while he pushed his little penis in and out of my vagina. There were grunts and groans like he'd trapped it in a door, and I can tell you, it was not the best of memories.

I have this fantasy about losing my virginity 'properly'. By this, I mean the man includes me in the love-making. I would also like a distinguished older man who knows how to push all the right buttons, not a young lout with no clue.

I went skiing recently, my first holiday without Mom and Dad. It was my first 'adult holiday' experience ─ finally free from family jail. This doesn't mean my home life was terrible; it simply feels like something is missing. I have no idea what, just 'something.'

The two girls who went with me on holiday were my best friends. We seemed to hit it off immediately when I arrived in the neighbourhood at the age of seven. We've since been in the same classes throughout our time in school. We had sleepovers at one another's houses at weekends and dabbled at cheerleading and stuff. We also shared secrets. My friends can also look at least three years older when they wear makeup.

We planned to be at the ski resort for five nights, arriving Sunday and leaving late Friday afternoon. Stupid timing, I know, but it made it less expensive. We had been saving hard all year for this holiday, so we wanted 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 a Friday and Saturday night stay as we paid for five nights. It didn't make sense because we wanted all our spare cash for partying and skiing.

After unpacking, we checked out the hotel dining room for dinner. The place was already half full of people who looked like they had been on the slopes all day. Many looked exhausted and would probably have an early night before hitting the slopes again in the morning.

Surveying the room, I reviewed the men to see if any rang my bell--a distinguished, single, older man. A quick room scan showed I wasn't in luck this time.

The hotel had an a la carte menu, but they also had a smorgasbord-style buffet, a fantastic array of food, just like college, but ten times better. The buffet came at a price far less than a la carte.

The three of us joined the line, with me at the rear. I saw what I'd fantasised about as he entered the dining room and joined the line behind me. He was in his late forties or early fifties, with grey hair at the temples and a tan that had taken a lot of sun time to achieve. He was over six feet tall and looked fit.

The man's broad shoulders and narrow waist did not go unnoticed. I think he'd spent a considerable time choosing his clothes; they were both smart and practical. The white edge of his turtle neck beneath his cashmere sweater had the logo of a well-known ski maker. This man was an identikit picture from my fantasy. He looked good enough to eat.

I turned toward the front of the line, a little embarrassed. While I wondered if he'd noticed my bitch-in-heat behaviour. He smiled and said, "Hi."

I replied, "Hello," like a startled idiot and rushed to my friends' table. I almost tripped and sat down with a thump. They could see I was flustered but couldn't work out the cause of the high colour in my cheeks. They checked to see why I was embarrassed but saw nothing suspicious.

When I got to my room later, I undressed, jumped into my nice warm bed and fantasised about my older man. When I closed my eyes, I imagined him inside me. I had an incredible, no-frills orgasm while masturbating.

Following a good night's sleep, we were on the road by 7.30. The weather was from a picture postcard, a great start to the holiday. I didn't know that my first-day skiing would end in less than three hours.

With no dedicated ski training, it didn't take too long for my thighs to begin aching. The stress of skiing the slope for the third time ended with my skis facing the wrong way and me sliding down the hill head-first. The powder snow made its way down my ass crack, and I couldn't stop shivering.

My ankle had taken a wrong turn, and my back felt like I'd strained muscles alongside my spine. I didn't feel on top of the world, but I thanked my lucky stars that it wasn't worse. I said the same thing aloud to my friends when they helped me to my feet. Feeling sore and embarrassed, I said I'd catch them later when they returned from the slopes.

When I arrived at the hotel, the staff helped me put away my ski gear. I decided to warm up with a coffee. As I entered the house bar, I saw my fantasy man from the evening before. He smiled, looked at my slight limp, and said, "Trouble on the slopes?"

"You could say that."

"What happened?"

I explained my lack of ski fitness and my stumble. I also explained that I'd decided to call it a day rather than chance making the injury worse. My fantasy man's name was Jeff, and he was in the bar enjoying a cappuccino because he'd been at the hotel a few days already and wanted a break from the snow and too many people.

After introducing myself, he suggested a hot bath and a warm oil massage. "You will feel a hundred per cent better after that, Lisa."

I didn't comment other than asking the barman for a coffee, thinking the recommended massage sounded fantastic.

We talked for the next half hour as though we'd been friends for a long time. It was nothing like my conversations with boys in college. I knew there was every chance my fantasy might come true if Jeff was as good at everything else as he was at holding a conversation.

Jeff explained that his wife had died two years earlier from breast cancer. They didn't have kids, so when she was gone, he was alone. He's relatively successful, fit, and lives in the same city where I live. His fitness came from daily visits to the gym and being an amateur triathlete on weekends. This week off was the first time he had stopped work long enough to take a holiday since his wife died. Burying himself in work was his way of getting over his grief.

It had taken him over a year to come to terms with life following his wife's death. There was no drama as he explained the situation; he told it how it was. He had not been with another woman 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 had said with a cheeky grin.

I didn't feel the slightest pressure from Jeff's comments; it made me think that he might be my fantasy come true. I decided I had better have the suggested hot bath, or the aches and pains would still be there tomorrow, cutting a large hole in my 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 the hotel doesn't have a masseur I could afford."

"Just call me when you've finished your bath, and I'll bring the oil. I'll be in room 571 when you're ready. I'm a pretty good masseur when I put my mind to it."

I smiled, said I might take him up on his offer and walked away as calmly as possible. My insides were doing backflips as I wondered whether I would call room 571 when I'd finished my bath.

When I returned to my room, I felt a chill. It was probably from seeing the snow outside the window. I turned the thermostat up ten degrees and began running the bath. A 'bath bomb' I'd brought from home had the foam a good foot above the tub before I knew what was happening. I thought about Jeff's offer as I stripped off my clothes.

Clouds of steam made the place warm as I stood in the bathroom. I waited a little while before jumping into the tub. It 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 massage offer. My body is aching, and I think trying to loosen up is a great idea. I'm in room 633; come up in half an hour. I'm about to jump in the bath, so I'll leave the door off the catch, and you can come straight in when you arrive."

"OK, see you in a half hour."

My heart began to thud like I'd been exercising hard. I heard my pulse loud in my ears. I returned to the bathroom, slipped out of the hotel-provided robe and stepped into the hot water. I lowered myself into the tub until the foam aligned with my eyes. I cleared a patch with my arm and lay back to enjoy the soak.

I heard the room door open and then close again a short time later. "It's Jeff, Lisa. I'm early; I hope that's OK?"

"Yes, of course. I'll soak a while longer, so please help yourself to a drink from the mini-bar."

"No need; I brought a bottle of bubbly with me. Would you like a glass while you soak?"

My heart picked up speed like a trip-hammer, and my imagination ran away with me because my pussy felt warm and wet inside ─ and out.

"Glasses are in the cupboard above the mini-bar."

A few minutes later, the bathroom door opened. Jeff stepped inside with a glass in both hands. He nudged the door closed and laughed when he saw the height of the foam above the bath water. "My God, what's happening? It's like Niagara Falls in here!"

I joined in with the laughter; the foam must have looked much higher from where he was. As I reached out to take the glass, I grabbed the side of the bath and then slipped. I dropped back quicker than I'd gotten up, and water cascaded over the side of the tub. I clutched the tub's surround to avoid losing the glass of bubbly.

I managed to hold onto the glass by sitting upright to regain my balance. Of course, the last thing I thought about was Jeff getting an uninterrupted view of me from the waist up.

"What do you do for an encore, Lisa?"

I looked at him and laughed. "I don't normally do this for visitors to my bathroom. You're the first and only one."

"I'm glad to hear that. Here, let me help you." He took the glass from my hand, placed it on the window sill, and helped me stand. Foam covered me from head to toe, so Jeff handed me a towel and returned to the main room with the glasses of bubbly. He placed them on the coffee table and returned to retrieve another towel from the rack.

I wrapped myself in the towel he'd handed me, then joined him in the bedroom. He had already placed the second towel across the bed and returned to the bathroom to run hot water over the bottle of massage oil. "OK, Lisa, loosen your towel at the front and relax on the bed while you're still warm. How are the aches and pains now?"

"I still feel very sore, so I'm looking forward to this massage."

As I unhitched the towel and lay across the bed, I noticed the bulge in Jeff's slacks. I don't know why I hadn't checked this before; he was, after all, my fantasy man. At first, I thought the bulge was a joke, like band members stuff socks down their pants before going on stage.

As I tried to relax face-down on the bed, I tilted my head and looked again. This time I could see the outline of his penis. It wasn't erect; it lay in a curve pointed toward his knee. I gulped and wondered what would happen with my fantasy -- during my massage.

When I was comfortable, Jeff removed the towel, folded it in half and placed it from waist to thigh. He went to the bathroom and returned with the warm oil. Relaxing my body was one thing, but relaxing my brain was another.

"Are you warm enough?"

"Yes, fine."

Jeff sat on the bed beside me and worked the oil into my shoulders and arms. I didn't know how to judge my feelings as Jeff's hands started the massage, but I knew how good it felt. 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 more comfortable. I heard myself say, "No problem, do whatever you need to." I looked around and saw Jeff take off his slacks and shirt.

He wore a white T-shirt and black boxers. Looking at his body made me close my eyes and think about the strong signals coming from my pussy. Jeff could now massage in a way that was better for him and far more exciting for me.

The first thing he did was come around to the end of the bed where my head lay and pull me further onto the bed. As he did this, I noticed that his flaccid cock had straightened out and taken on the shape of a salami. I can't be sure, but I could have sworn I saw the tip of it poking out from the leg of his boxers.

Jeff went to the end of the bed where my feet lay, and without speaking, he straddled my legs and began working on my back with solid strokes. It felt wonderful. What Jeff was doing to me with his fingers was starting to get me excited and wet. I couldn't believe it; this guy would soon make me orgasm by touching my back and shoulders. I was getting so hot I started to grind my pubic bone into the bed with slow gyrations.

Suddenly Jeff slid his hand under the towel and lightly stroked my ass. I rose onto one elbow and looked at him. He smiled at me and said, "Everything OK?"

I nodded, and my lips parted. Jeff poured oil from the bottle into my ass crack. He then put the bottle away and rubbed my ass with one hand while the other stroked the sensitive bridge between my asshole and pussy. I didn't know where the moaning noises were coming from until I realised it was me.

After sliding his fingers up and down the lips of my pussy his fingers slid down my legs until they reached my feet. He kept an even amount of oil on all parts of my body without it feeling uncomfortable.

Jeff asked if I would turn over following my leg and foot massage. I didn't reply; I just turned over and returned to where I'd lay when I was on my front. Jeff refolded the towel and covered my lower half again while my top half remained naked. I thought Jeff would begin at my breasts, but he didn't; he started at my fingertips.

He massaged each finger in turn, then my hands, arms and shoulders, before making large circles with his fingers on my breasts. By this stage, my pussy was so wet I could swear my juices must be running down my leg. My nipples and dark areola were more prominent than I had seen before ─ and when Jeff gently pinched the nipples, I became more aroused than I'd been in my life.

Once again, Jeff's hands delved below the towel and rubbed oil into the top of my thighs and pussy, this time from the front, not the back. My legs opened wider of their own accord. First one, then two of Jeff's fingers slid inside my pussy. As a third finger slipped in beside these, I felt a wonderful pressure building. I knew I was within a whisker of orgasm.

The areas to each side of my neck tingled, and then my ears felt hot. The slippery noise of oiled fingers darting in and out of my pussy seemed far away. The heat I felt below my jawline reached my nipples and rushed across my stomach. Jeff's thumb rubbed my swollen clitoris, and the three fingers continued their ministrations. I knew I would have a spectacular orgasm before this man put his cock anywhere near me.

Finally, the orgasm burst over me like a dam breaking free. I don't know if I screamed or just moaned. I know it felt like my nerve endings were vibrating at supersonic speed. I don't recall ever having feelings like this.

Moments after my orgasm, Jeff's legs moved from where he'd straddled my legs to a position beside the bed. He massaged my pussy lips with one hand and then stopped to lift his T-Shirt over his head. I stared as he slowly removed his boxers and asked if I was enjoying the massage. I said, "Mmmmmm," and continued to stare in disbelief.

The size of his cock was hard to describe. I've seen porno on the internet where a guy is said to have a twelve-inch cock. I can only presume they must have taken their measurements from the guy's asshole to the tip because there is no way they were the length they claimed.

Jeff's cock was huge. What hung between his legs was bigger than any I'd seen before. I put my hands out and grabbed it at the base. I squeezed it but still couldn't get my hand to close around it. I was at least an inch shy of my fingers meeting, and it wasn't fully erect; it was hard to believe there was still room for growth.

Jeff lifted my head and kissed me. Our tongues met and danced with one another. I felt my next orgasm building in the wings. We briefly separated, with Jeff's cock only inches from my face.

I pulled his cock toward my mouth, and Jeff moved toward me with the pressure from my hands. Opening my mouth as wide as it would go, I forced my lips over the knob. It seemed to fill my entire mouth. I made more saliva as I sucked and slid my hands along the shaft. Jeff moaned in ecstasy. His cock was like a steel spike, and as my tongue produced more saliva, I squeezed enough of him into my mouth that the tip touched the back of my throat. Although he filled my mouth, there was still more outside.

Jeff tried to withdraw, but I held him steady, in control. After a while, there was a loud 'plop' as he exited my mouth, and the towel covering my pussy and thighs dropped to the floor. He dragged me toward the edge of the bed, then pushed my legs toward my head and outwards. I felt my pussy lips unfurl like rose petals.

A hot tongue licked my pussy toward my second orgasm, and as Jeff's mouth closed around my clitoris, my arms dropped by my side in surrender to sensual overload.

When Jeff pulled me closer to the edge of the bed, I reached down to guide him into my soaking wet pussy. He pushed forward, and my pussy lips stretched further apart than ever before. The relief when they eventually closed around the knob end was intense.

He slowly pushed into my vagina in small increments. I thought I would burst, but Jeff settled into a slow rhythm and was soon balls deep. The fit was tight, and each time he withdrew, I could see my pussy clinging to his shaft. The sight was incredibly arousing; I started coming again and shoved my hips against each of his thrusts. I reached the most incredible climax imaginable. I thought the first two orgasms I had experienced were something else, but this made the others feel like a brief practice session.

I didn't think I could take more of this exquisite torture, but by now, I was saturated, and Jeff penetrated even deeper into my flesh-pink tunnel. I let out one low continuous groan as I watched inch after inch disappear into me in one fluid motion. I didn't think it possible, but soon my pussy wrapped his entire length, and Jeff momentarily stopped thrusting. He let his cock throb inside me and watched my face as my fourth climax formed. I couldn't help it; I started thrashing beneath him. His chest squashed my breasts, the oil making wonderfully obscene noises. "I have never been fucked like this before, Jeff. Not even in my wildest dreams. Please don't stop."

Soon, we both cried out, "I'm coming!" As we ground into each other, I felt the pressure of his semen shoot up high inside me repeatedly. I watched Jeff's face as his orgasm exploded, and the look on his face was incredible, the battle between emotions in a sensual war.