Quickie: Ride of a Lifetime

** Thanks to Deadeye for the edits**

I took a year off school after graduation. Having just turning nineteen, I figured I'd put a year of work in, have fun, and then start college the following year. This gave me plenty of time to hang with friends, work, and enjoy some of my favorite things, including cycling and working out.

I'm not a very big guy so climbing mountains on my bike kind of comes naturally. I look for new hills to climb, the steeper the better, as long as it's paved. I don't do much mountain biking, its mainly the road for me.

It was around the start of July and I had a lot of miles behind me on the bike. I was in really good shape from all the climbing, but I was getting kind of tired of the same climbs day after day. So, I decided to leave the main road and take the exit to a small mountain town and see what I could find in the way of climbs on the back roads.

It was a beautiful July day, already getting hot, which I don't really mind. There was not a cloud in the sky as I pedaled through the small town, following the main road toward the rising mountains before me. Luckily the road stayed paved and the climbing began in earnest. I was hoping it would continue for as long as possible, because a lot of roads like this usually turn to dirt quickly, but so far so good as the incline continued steadily upwards.

I noticed that the houses were huge and very spread out, probably one every mile or so and very nice. I was definitely in a wealthy area, probably why the pavement continued as long as it did. I was about five miles up the climb when it really kicked up, probably the steepest I've ever climbed on my road bike, and I had to shift down to the lowest gear and stand up to make it. This made me gleeful actually, I had found a new climb, a very steep climb, and I was thrilled.

But everything comes to an end, even a good climb, and I saw that the road ended up ahead in front of a large gate and mansion. I road all the way to the gate, which was about eight feet tall, and saw that it had a keypad entry and a couple of cameras pointing down at me. I stopped, breathing very heavy from the incredible incline and stood there, straddling my bike as I took a break, before descending back down the way I came.

I was looking through the gate, checking out this enormous house and yard, and wondered who lived there. How much money would you have to have to own something like this place? Suddenly the gate started opening, swinging inward right in front of me. I expected someone's voice on the keypad speaker or something but heard nothing. The gate just opened. I figured, what the hell, I'll go and get a better look at the place. I mounted my bike and pedaled in, riding up the lavish drive toward the house, checking out the meticulous yard until I arrived at the front entry. The road continued on around the side of the house, I figured the garage was at the end, but I stopped at the front doors.

I don't know what I expected; I was dressed in tight spandex, clipless biking shoes, a helmet, and fingerless gloves, standing over my bike staring at the huge doors to probably the biggest house I'd ever seen. I didn't know why the gate opened for me or if I should go and knock or just get back on my bike and head down the mountain.

I gave it another half a minute and then clipped back into my pedals and turned to go, when I heard a woman's voice say, "Don't go!"

I looped around and rode back to the doors, one of which was now open, and standing in the doorway was a woman, a very beautiful woman. She was older than I was, by at least ten years, probably more, but she was very attractive. Long brown hair, incredible face, and an even better body. She was only wearing a sports bra and tight workout shorts. I could tell she had been exercising, her long hair was in a tight ponytail and her tan skin had a light sheen of perspiration, making her almost shine.

"Hello," I said.

"Hello, my name is Madison. I saw you outside the gate, having rode all the way up that steep hill and thought you might want some water," she said.

"Sure, I could fill up my bottles, I guess. Your house is amazing," I said, trying to keep my eyes on hers since her large breasts were all but popping out of her tight, low cut sports bra.

"Want to come inside? You can leave your bike here in the foyer... umm... what should I call you?"

"Oh, sorry. Jase; my name is Jase and I guess I can come in."

"Jase? Is that short for Jason?" she asked as she moved out of the way for me to pass into the foyer.

"No, just Jase. It's what my parents named me."

"I see, well Jase, leave your bike there and probably your shoes as well," she said, seeing me walking funny and making clomping noises as my cleated road shoes met her tiled floor.

The first thing I noticed was how quiet and empty the huge house was as I followed Madison on my stocking feet, holding both of my water bottles.

"You all alone in this giant house?" I asked.

"Today, yes. My husband is on a business trip and the servants and yard crew only come once a week.

"Wow, this place is huge!" I said, looking around.

"Want a tour? I don't get very many visitors, especially when Ryan is out of town."

I assumed Ryan was her husband, who was one lucky son-of-a-bitch. Walking behind Madison was a treat to behold. She had an incredible ass, long toned legs, and a sexy back. I could see most of her with her only in that ponytail, workout shorts, and sports bra. I didn't have to be anywhere so I accepted the tour which started in the kitchen to allow me to fill up my water bottles.

"You can leave them in the fridge while I show you the house," she said, opening a huge stainless-steel fridge that you'd normally only see in a massive restaurant.

I put my water bottles in and turned back to her; she was looking at my ass and biting her lower lip as I turned around. I pretended I didn't notice.

"Where to first?" I asked.

"Follow me," she said.

I wanted to say, 'my pleasure' but didn't, I just smiled and Madison headed out of the kitchen to show me the rest of the house. It was in one of the living rooms where I saw a large photo of her standing behind some old dude sitting in a chair.

"Who's that you're with, your grandpa?" I asked.

"No, silly, that's Ryan, my husband. I'll admit there is a bit of an age difference."

"Your husband? Oh, wow," I said, before thinking that Madison was definitely a trophy wife. He looked twice her age and the picture seemed pretty recent.

"He treats me really good; I have everything I want," she said motioning to the house. "Well, almost everything," I heard her say under her breath.

We continued the tour and I found myself watching her ass more than the house. She showed me room after room with the nicest stuff money can buy. The garage was insane, her husband had a huge car collection the likes of which I'd only seen at a car show. I was blown away. We ended up in the gym with a full workout room, sauna, pool, hot tub, the works, even a tanning booth. I also noticed in one corner of the gym a complete massage set up with table, chair, and cabinets.

All of this walking without stretching after my climb had my legs tight and I felt a cramp coming on in the coolness of the gym. I groaned a little, rubbing my legs and Madison noticed.

"That climb up here has made your legs sore. Lay down on the massage table and I'll work on them for you." she offered.

I figured what the heck, and laid face down on the massage table, not thinking about the consequences of Madison touching me and rubbing my legs. She started low on my calves after peeling off my socks and worked upward to my hamstrings and even higher toward my butt. That's when the problem began. My nineteen-year-old penis sprung to life in my tight bike shorts as she rubbed my legs. I didn't know what to do; I couldn't move because she was sure to notice my erection in the tight shorts if I rolled over or got up.

"Before I met Ryan, I was a massage therapist; that's why all this stuff is here. It's actually how we met. I was working at one of his office buildings, giving massages to his employees, and that's when we first met each other and just hit it off," she was saying as she worked my legs.

I could tell she knew what she was doing and so could my dick. If anything, it was getting harder instead of tapering down.

"Okay, flip over and I'll do the other sides," she said, after finishing the back of my legs.

"Umm, I can't?" I said.

"Why? What's wrong?" she asked.

"I seem to have a little problem... with my shorts," I said.

"What? They look fine... oh... I see." she said.

"Yeah, this is embarrassing. I'm going to need a few minutes," I said.

"I'm sorry. I didn't realize what might happen. I'm not used to it being so easy... or even possible?" she said.

"What do you mean?" I asked.

"Ryan... well... you saw the picture. He's well into his seventies and... well, to put it bluntly he can't manage anymore," she said.

"Oh. I'm sorry," I said.

"Someone your age wouldn't know anything about that," she added.

My dick was still hard, throbbing actually, and I didn't really know what to say or do with her standing next to the massage table talking about her husband's erectile dysfunction. She went on about how it's been several years since Ryan was interested in or able to have sex, even with pills. She said she missed it on occasion, when she wasn't entertaining, busy with charity work, the book club, and the like. I was hoping the time would help my erection subside but it didn't. It was kind of locked in even with her not touching me anymore.

After about five to ten minutes of her talking and me nodding, she asked, "Ready? Can you turn over now?"

"Umm... not quite yet," I said, with just as large an erection as ten minutes ago.

"Really? Still? Well, I can promise not to look or maybe close my eyes to finish massaging your legs," she said.

"That would only make it worse," I said.

"Oh, my, Jase you have me at a disadvantage. I'm blushing and feel a little flushed... it's been so long... may I possibly see it?" She asked, hesitantly.

"See it... with the shorts off?" I asked.

"If that's okay?" she asked again. "I could give you a better massage without them anyway."

"It's nothing to get excited about," I said.

"Oh, I'm sure that's not true. Really, Jase, if it's erect it will be better than I've seen in years."

Holy fucking shit, I thought to myself. This incredibly hot woman, starved for sex, wanted to check out my boner; maybe more. It was the least I could do for her after she was so nice. I wasn't ashamed of my body; I knew I was in incredible shape from all the lifting and cycling.

"Okay, sure. If you want," I said, turning over and hooking my thumbs under my tight shorts.

I pulled them down over my dick and watched the expression on Madison's face. She looked like a little girl on Christmas morning, the smile just kept growing and her face lit up like she had opened the best present in the world.

"Oh, my... so hard. It's nothing to be ashamed of, Jase. It's a very nice-looking penis," she said.

"Yeah, I guess... not very big, but it does get really hard."

She stood there, looking at my hard penis for several minutes. I noticed her nipples get hard under her sports bra as she looked at me. I kicked off my bike shorts, and took off my jersey as well, which got her attention again.

"I'll finish massaging your legs; it will be easier now," she said admiring my naked body.

She opened a cabinet next to the table I was lying on and reached in. She turned around with a bottle of oil. She uncapped it, poring some in her hands and dripping it down on my legs. It got warm fast as she rubbed it into my flesh. She started working my legs, hands sliding much better with the oil. I just laid there, enjoying her massage with my cock fully hard and oozing as she worked. It felt really good and really worked out any cramps I had.

As she worked, I couldn't help but notice that she kept her eyes more on my penis than whatever she was touching. She watched it pulse to my heartbeat and even ooze, dripping down to my stomach. When she was done with my legs she moved toward my waist, staring down at my penis.

"You've oozed quite a bit while I massaged your legs, Jase, do you need me to release some pent-up pressure?" she asked.

She was shaking, at least her hands, holding the bottle of oil. I could tell she was excited or nervous; it truly had been a long time for her.

"You're suggesting making me ejaculate with your hands?"

"Yes, if you would like. It's been such a long time since I've touched a hard penis. Would you allow me to?" she asked.

"Okay, sure, if you want," I said.

Her hands were really shaking now, and her nipples were hard again. She was really worked up. When she tried to pour some oil in her hands, it spilled out fast, splashing down onto my cock and stomach. She giggled and apologized before setting the bottle down. Madison reached slowly for my penis, laying her palm down on my shaft, causing me to suck in a deep breath at the first contact. She rubbed up and down my rigid shaft with the palm of her hand, moving the oil around before sliding up to the head and then rotating her hand palm up and gripping me with her fingers.

She lifted my hard dick almost vertical and I could see the pleasure it caused on her face as she slid her hands down my shaft and then back up for the first full stroke. It felt amazing! Her other hand joined in, rubbing oil around my already tightening balls, kneading the loose skin and rolling them in her palm as the first hand stroked up and down slowly.

"It's so firm... such constant blood flow. It's a marvel," she said, admiring my erection as she stroked.

I had felt nothing like it before; the oil, her expert hand. I thought I had died and gone to handjob heaven. She continued to play with my balls and now was palming my engorged head, rubbing her oiled palm around and around, causing my toes to curl at the intense sensation, before stroking again. Two different sensations, both incredibly satisfying.

The stroking made me want to cum and the head teasing was so intense I didn't know what would happen if she continued, but it kept me from cumming until she started stroking again. I was humming with pleasure, going back and forth from being on the verge of ejaculation to toe curling head teasing for several minutes. My heart was pounding like I was climbing the hill to her house again.

"Do you want to cum?" she asked after another several minutes of pure pleasure mixed with an almost painful desire to cum.

"Yes, please!" I said, my back arched and my legs tight.

I don't think I'd ever wanted to cum so badly in my life. The way she brought me to the edge before stopping and working my head, had me more worked up than I'd ever been in my life. My balls were so tight they almost hurt from want of release, so when she asked me if I wanted to cum, I practically screamed for it.

She stopped spinning her palm around my head and began to stroke again. My balls were so tight, she could only rub them as they snuggled up to my shaft. She sped up with the stroking, holding my shaft slightly tighter and I was on the verge seconds later, exploding the next. A huge rope of cum shot into the air and came splashing down on my body as the second blast was already in the air. She stroked and stroked through my orgasm as I splattered cum all over her hand, arm and my body from my chest to my legs as the cum flew in different directions, depending on the position of my head when the shot came.

"So much semen... so potent... so young and virile. Amazing!" she called out as my cock ejaculated like a geyser.

I had never felt an orgasm like this. The buildup, the talent, her being in control; all of it mixed together to give me a mind-blowing climax my young body had not experienced before. It rocked me, leaving me totally limp and covered in my semen when she was done.

**

I lost track of time for a minute; might have even drifted off after such a massive orgasm. When I was aware of my surroundings again, there was a towel over my limp penis and Madison was nowhere to be seen. I sat up, looking around the large gym, and didn't see her until I looked closer at the hot tub. She was sitting in the water, probably naked. I cleaned my body off, wiping up the large load and turned to stand up. My legs were wobbly from the ride and the climax, but I managed to support myself and headed in her direction.

"Care if I join you?" I asked, walking to the side of the tub.

"Please," she responded.

She was naked for sure, since her shorts and sports bra were discarded next to the hot tub. The water was rolling and bubbling between her breasts and I really couldn't see much of her incredible body yet. I eased into the hot water, a couple of feet down from her.

"Come closer; sit next to me," she said.

I scooted closer until my body hit her hips under the water.

"Do you know why I opened the gate, Jase?" she asked.

"I think I'm beginning to," I responded.

"It wasn't for you to get water. I saw you, so young, so in shape, and I acted out of impulse and opened the gate. I almost let you just ride away, but seeing you leaving, I threw open the door and called for you. I'm so lonely... so horny, Jase... my husband is too old to pleasure me now. I opened the gate for you to fuck me!" she blurted. "Will you... fuck me?"

I turned toward her, reaching my hand out to her arm, sliding it up to her shoulder and toward her neck. I did the same with the other hand and then with both of them together on her neck, slid them down her upper chest to her firm round breasts. My young dick sprang back to life and I felt her nipples pressing out on my palms as I gently caressed her perfect breasts under the water.

"Oh, Jase, that feels so nice. I want you so badly I can hardly sit still," she said.

I didn't want to stop touching her breasts. They were amazingly firm and her nipples got so hard under my palms that it was easy to pinch and tug on them with my thumb and fingers, making her moan and coo from the sensations. Sliding one hand down her flat stomach, she spread her legs as I neared her sex. I found her completely shaved as my fingers slid over her pubic bone and down to the beginning of her folds. Her fleshy lips wiggled in the moving water as I cupped her sex and dug two fingers into her water washed vagina.

She practically screamed with pleasure when I dug in deeper and curled my fingers back toward the entrance inside of her. My thumb found her little engorged clit easily, it was almost as hard as her nipples. Pressing on her clit with my thumb, I ground my fingers inside of her as my other hand pinched her left nipple.

"Oh, shit Jase. You're driving me crazy. I'm... I think I'm going to cum!" she voiced and moaned as I continued fingering her.

She was obviously pent up and majorly horny to cum so easily as I stroked her, but cum she did, squeezing my hand with her toned thighs as the climax flooded her body. She started shaking and I tried my best to continue to finger her as she squirmed and spasmed in the hot water.

My dick was fully hard again from touching this incredibly hot woman and making her cum in the tub. When she stopped cumming, I removed my hand from her sex and let her gather her composure. She opened her eyes and looked at me.

"That was nice but I still want to feel you inside me," she said, moving quickly toward me.

She threw her left leg over mine and climbed right up on my lap in the hot water. This gave her enough height for me to finally be able to see her breasts and holy shit it was worth it. I'd never seen a more perfect pair in my life and I just stared at them as she sat on my lap. She noticed since I wasn't moving or trying to get my cock into her.